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[ CAS No. 408492-28-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Chemical Structure| 408492-28-4

Chemical Structure| 408492-28-4

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Quality Control of [ 408492-28-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 408492-28-4 ]

CAS No. :	408492-28-4	MDL No. :	MFCD09953498
Formula :	C₁₂H₁₆BIO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HSHFNMSHDHAHDN-UHFFFAOYSA-N
M.W :	329.97	Pubchem ID :	11313483
Synonyms :

Safety of [ 408492-28-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P273-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302-H413	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 408492-28-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 408492-28-4 ]
Downstream synthetic route of [ 408492-28-4 ]

[ 408492-28-4 ] Synthesis Path-Upstream 1~1

1
[ 408492-28-4 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8408 - 8411

[ 408492-28-4 ] Synthesis Path-Downstream 1~50

1
[ 626-00-6 ]
[ 1195-66-0 ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 1,3-Diiodobenzene With TurboGrignard In tetrahydrofuran at -20℃; for 1h; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -20 - 20℃;

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

2
[ 408492-28-4 ]
[ 56671-82-0 ]
3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclohex-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane With TurboGrignard In tetrahydrofuran at -78℃; for 1h; Stage #2: In tetrahydrofuran at -78℃; for 0.5h; Stage #3: 3-Iodocyclohex-2-enone In tetrahydrofuran at -78 - 20℃;

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

3
[ 408492-28-4 ]
[ 56671-84-2 ]
2-methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohex-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane With TurboGrignard In tetrahydrofuran at -78℃; for 1h; Stage #2: In tetrahydrofuran at -78℃; for 0.5h; Stage #3: 3-iodo-2-methylcyclohexenone In tetrahydrofuran at -78 - 20℃;

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

4
[ 408492-28-4 ]
[ 100-52-7 ]
[ 857934-89-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane With TurboGrignard In tetrahydrofuran at -78℃; for 1h; Stage #2: benzaldehyde In tetrahydrofuran at -78 - 20℃;

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

5
[ 408492-28-4 ]
[ 638-29-9 ]
1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pentan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane With TurboGrignard In tetrahydrofuran at -78℃; for 1h; Stage #2: In tetrahydrofuran at -78℃; for 0.5h; Stage #3: n-valeryl chloride In tetrahydrofuran at -78 - 20℃;

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

6
[ 76-09-5 ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 68 percent / 2 h / 68 °C 2.1: iPrMgCl*LiCl / tetrahydrofuran / 1 h / -20 °C 2.2: 88 percent / tetrahydrofuran / -20 - 20 °C

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

7
[ 408492-28-4 ]
[ 807329-97-1 ]
BO₂(C(CH₃)2)2(C₆H₄MgCl) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran reaction of BO2(C(CH3)2)2(C6H4I) with i-PrMgCl*LiCl in THF at -78°C, 2h;

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

8
[ 408492-28-4 ]
[ 807329-97-1 ]
[ 56671-84-2 ]
2-methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohex-2-enone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In not given BO2(C(CH3)2)2(C6H5I) treated with iPrMgClLiCl at -78°C for 1h; addn. of CuCN2LiCl; addn. of 3-iodo-2-methylcyclohexenone at -78°C; warming to room temp.;

Reference： [1]Baron, Oliver; Knochel, Paul [Angewandte Chemie - International Edition, 2005, vol. 44, # 20, p. 3133 - 3135]

9
[ 408492-28-4 ]
[ 914362-04-2 ]
[ 32316-92-0 ]
[ 1082605-91-1 ]
[ 1082605-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane; naphthalene-2-boronic acid With sodium carbonate In water; toluene at 80℃; for 6.5h; Stage #2: 3,4-dibromo-5-[(2-methoxyethoxy)methoxy]-5H-furan-2-one With tetrabutylammomium bromide; cesium fluoride In tetrahydrofuran; water at 120℃; for 0.0833333h; microwave irradiation; Further stages.;

Reference： [1]Aquino, Maurizio; Guerrero, Maria D.; Bruno, Ines; Terencio, Maria C.; Paya, Miguel; Riccio, Raffaele [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 9056 - 9064]

10
[ 408492-28-4 ]
[ 51067-38-0 ]
[ 1082606-06-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium carbonate In water; toluene at 80℃; for 7h;

Reference： [1]Aquino, Maurizio; Guerrero, Maria D.; Bruno, Ines; Terencio, Maria C.; Paya, Miguel; Riccio, Raffaele [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 9056 - 9064]

11
[ 408492-28-4 ]
[ 32316-92-0 ]
[ 1082606-07-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate In water; toluene at 80℃; for 6.5h;

Reference： [1]Aquino, Maurizio; Guerrero, Maria D.; Bruno, Ines; Terencio, Maria C.; Paya, Miguel; Riccio, Raffaele [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 9056 - 9064]

12
[ 408492-28-4 ]
[ 113893-08-6 ]
[ 1082606-05-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium carbonate In water; toluene at 80℃; for 6h;

Reference： [1]Aquino, Maurizio; Guerrero, Maria D.; Bruno, Ines; Terencio, Maria C.; Paya, Miguel; Riccio, Raffaele [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 9056 - 9064]

13
[ 76-09-5 ]
[ 221037-98-5 ]
[ 408492-28-4 ]

Reference： [1]Patent: JP2019/182779,2019,A .Location in patent: Paragraph 0316; 0326
[2]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9056 - 9064

14
[ 626-01-7 ]
[ 73183-34-3 ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With tert.-butylnitrite In acetonitrile at 80℃; for 2h;

Reference： [1]Qiu, Di; Jin, Liang; Zheng, Zhitong; Meng, He; Mo, Fanyang; Wang, Xi; Zhang, Yan; Wang, Jianbo [Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933]

15
[ 626-01-7 ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrafluoroboric acid / water / 0.17 h / 0 °C 1.2: 1 h / 0 °C 1.3: 2.5 h / 20 °C / Inert atmosphere 2.1: diethyl ether / 4 h / 20 °C
	Multi-step reaction with 3 steps 1.1: tetrafluoroboric acid / water / 0.17 h / 0 °C 1.2: 1 h / 0 °C 1.3: 20 °C / Inert atmosphere 2.1: 1 h / 0 - 20 °C / Inert atmosphere 3.1: diethyl ether / 4 h / 20 °C / Inert atmosphere

Reference： [1]Marciasini, Ludovic D.; Richy, Nicolas; Vaultier, Michel; Pucheault, Mathieu [Advanced Synthesis and Catalysis, 2013, vol. 355, # 6, p. 1083 - 1088]
[2]Marciasini, Ludovic D.; Vaultier, Michel; Pucheault, Mathieu [Tetrahedron Letters, 2014, vol. 55, # 10, p. 1702 - 1705]

16
[ 76-09-5 ]
C₁₂H₁₉BIN [ No CAS ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at 20℃; for 4h;

Reference： [1]Marciasini, Ludovic D.; Richy, Nicolas; Vaultier, Michel; Pucheault, Mathieu [Advanced Synthesis and Catalysis, 2013, vol. 355, # 6, p. 1083 - 1088]

Yield	Reaction Conditions	Operation in experiment
70%	In diethyl ether at 20℃; for 4h;	26 General procedure B: tandem diazotation/borylation sequence of aniline to aryl boronate General procedure: To a solution of aniline (1 mmol) in 3 ml of distillated acetonitrile, at 0°C, is added boron trifluoride etherate (1.5mmol 0.4 ml) and the solution is stirred for 5 minutes. Isoamyl nitrite (1.2 mmol, 0.2 ml) is then slowly added and thesolution is stirred for 15 minutes. Diisopropylamino borane (4 mmol, 0.6 ml) is then slowly added and the mixture isallowed to be stirred at room temperature for 3 hours. The reaction is then quenched, at 0°C, by the slow addition of 2ml of distillated methanol and stirred 1 hour at room temperature. The mixture is concentrated under vacuum and asolution of pinacol (1.3 mmol, 153 mg) in 2 ml of diethyl ether is added and the mixture is stirred 4 hours at roomtemperature. 10 ml of diethyl ether is then added and the crude is washed three time with 6 ml of a aqueous solution of copper chloride (50 g/L). The organic phase is then filtered and died over Na2SO4 and concentrated under vacuum toafford pure aryl boronate. 113 mg of 2-(4-methoxy-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were obtained following the generalprocedure B using 123 mg of 4-methoxyaniline as a pale yellow oil, yield: 52.5%. 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J= 8.7 Hz, 2H) 6.90 (d, J= 8.7 Hz, 2H) 3.83 (s, 3H) 1.33 (s, 12H). 11B NMR (100 MHz, CDCl3) δ 31.0513C NMR (75 MHz, CDCl3) δMS (EI) tR= 9.05 min; m/z: 234 (M+., 100%)

18
[ 76-09-5 ]
3-iodobenzenediazonium tetrafluoroborate [ No CAS ]
[ 22092-92-8 ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 3-iodobenzenediazonium tetrafluoroborate; diisopropopylaminoborane With ferrocene In acetonitrile at 20℃; for 2.5h; Stage #2: With methanol In acetonitrile at 0 - 20℃; for 1h; Stage #3: 2,3-dimethyl-2,3-butane diol In diethyl ether; acetonitrile at 20℃; for 4h;	26 Example 26: synthesis of 2-(3-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [CAS 408492-28-4] , compound VI_A23. Example 3: General procedure D for the synthesis of the arylpinacolboronates by arylation of diisopropylaminoborane, catalysed by ferrocene (1%), followed by methanolysis and transesterification In a dried tube reactor under argon as described in example 2, the arenediazonium salt (1 mmol) and the ferrocene (ΙΟμιηοΙ, 1.8mg) were dissolved in 2mL of anhydrous CH3CN. Diisopropylaminoborane (2mmol, 226mg) was then added to the solution and the mixture was stirred for 2h30 at room temperature. The reaction mixture was quenched by a slow addition of anhydrous MeOH at 0°C (2mL) and stirred for an additional hour at room temperature. After removal of all the volatiles, 1.3eq of pinacol was added in Et20 (2mL), the mixture was stirred 4h at room temperature. The crude mixture was washed with a 50g/L CuCl2 solution (2 x 5mL). The organic layer were separated, dried over Na2S04, filtered and concentrated to dryness. The resulted oil was dissolved with CH2C12 and filtered of a pad of silica gel, eluting with CH2C12 to afford the corresponding boronate. Example 26: synthesis of 2-(3-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [CAS 408492-28-4] , compound VIA23. 230 mg of 2-(3-iodophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane were obtained following the general procedure D according to example 3, using 318mg of 3-iodobenzenediazonium tetrafluoroborate as a pale yellow oil, with an isolated yield of 70%. 1H NMR (300 MHz, CDC13) 5 8.14 (s, 1H) 7.74-7.80 (m, 2H) 7.11 (t, J = 7.6 Hz, 1H) 1.34 (s, 12H) nB NMR (100 MHz, CDC13) δ 30.2 13C NMR (75 MHz, CDC13) δ 25.0; 31.1; 84.3; 94.4; 129.8; 133.8; 140.2; 143.6 GC-MS (EI) tR= 9.80 min; m/z: 330 (Μ+·, 100%)

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF BORDEAUX 1 - WO2014/9169, 2014, A1 Location in patent: Page/Page column 64

19
[ 76-09-5 ]
C₈H₁₀BIO₂ [ No CAS ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether at 20℃; for 4h; Inert atmosphere;	GENERAL PROCEDURE D FOR THE SYNTHESIS OF THE ARYL BORONATES WITH ZIRCONIUM CATALYST General procedure: In a dried tube reactor under argon, were dissolved the diazonium salt (1 mmol) and zirconocene chloride hydride (Schwartz’s reagent) (10μmol, 2.6mg) in 2mL of anhydrous CH3CN. Diisopropylaminoborane (2mmol 226mg) is then added to the solution and stirred for 2h30 at room temperature. The reaction mixture is quenched by a slow addition of anhydrous MeOH at 0°C (2mL) and stirred for an additional hour at room temperature. After removal of all the volatiles, 1.3eq of pinacol is added in Et2O (2mL), the mixture is stirred 4h at room temperature. The crude mixture is washed with a 50g/L CuCl2 solution (2 x 5mL). The organic layer is separated, dried over Na2SO4, filtred and concentrated to dryness. The resulted oil is dissolved with CH2Cl2 and filtered of a pad of silica gel, eluting with CH2Cl2 to afford the corresponding boronate.

Reference： [1]Marciasini, Ludovic D.; Vaultier, Michel; Pucheault, Mathieu [Tetrahedron Letters, 2014, vol. 55, # 10, p. 1702 - 1705]

20
C₁₂H₁₉BIN [ No CAS ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1 h / 0 - 20 °C / Inert atmosphere 2: diethyl ether / 4 h / 20 °C / Inert atmosphere

Reference： [1]Marciasini, Ludovic D.; Vaultier, Michel; Pucheault, Mathieu [Tetrahedron Letters, 2014, vol. 55, # 10, p. 1702 - 1705]

21
[ 408492-28-4 ]
[ 6258-60-2 ]
2-(3-(4-methoxybenzylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine; (1,2-dimethoxyethane)dichloronickel(II); Ir[dF(CF₃)ppy]2(dtbbpy)PF₆; 4,4′-di-(tert-butyl)-2,2′-bipyridyl In acetonitrile at 23 - 25℃; for 24h; Irradiation; chemoselective reaction;

Reference： [1]Oderinde, Martins S.; Frenette, Mathieu; Robbins, Daniel W.; Aquila, Brian; Johannes, Jeffrey W. [Journal of the American Chemical Society, 2016, vol. 138, # 6, p. 1760 - 1763]

22
[ 408492-28-4 ]
[ 73183-34-3 ]
[ 365564-05-2 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 8408 - 8411

23
[ 408492-28-4 ]
[ 1071-46-1 ]
[ 90888-00-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With copper(II) bis(trifluoromethanesulfonate); triethylamine In N,N-dimethyl acetamide at 20℃; Sealed tube;

Reference： [1]Moon, Patrick J.; Yin, Shengkang; Lundgren, Rylan J. [Journal of the American Chemical Society, 2016, vol. 138, # 42, p. 13826 - 13829]

24
[ 408492-28-4 ]
[ 108-44-1 ]
3-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With (1,2-dimethoxyethane)dichloronickel(II); Ir[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]₂(4,4'-di-tert-butyl-2,2'-bipyridyl)PF₆; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 23 - 25℃; for 24h; Sealed tube; Irradiation; chemoselective reaction;

Reference： [1]Oderinde, Martins S.; Jones, Natalie H.; Juneau, Antoine; Frenette, Mathieu; Aquila, Brian; Tentarelli, Sharon; Robbins, Daniel W.; Johannes, Jeffrey W. [Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13219 - 13223][Angew. Chem., 2016, vol. 128, # 42, p. 13413 - 13417]

25
[ 408492-28-4 ]
[ 24395-14-0 ]
(S)-4-methyl-N-(2-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane; N-(p-tolylsulfonyl)-2-phenylaziridine With manganese; sodium iodide In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: With chloro-trimethyl-silane; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole In tetrahydrofuran at -10℃; for 72h; Inert atmosphere; Sealed tube; enantioselective reaction;
63%	With manganese; chloro-trimethyl-silane; (1,2-dimethoxyethane)dichloronickel(II); (4S,4'S)-(4,4'-diheptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole; sodium iodide In tetrahydrofuran at -10℃; for 72h; Sealed tube; Inert atmosphere; enantioselective reaction;

Reference： [1]Woods, Brian P.; Orlandi, Manuel; Huang, Chung-Yang; Sigman, Matthew S.; Doyle, Abigail G. [Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5688 - 5691]
[2]Woods, Brian P.; Orlandi, Manuel; Huang, Chung-Yang Dennis; Sigman, Matthew S.; Doyle, Abigail G. [Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7744 - 7745]

26
[ 408492-28-4 ]
[ 24395-14-0 ]
4-methyl-N-(2-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane; N-(p-tolylsulfonyl)-2-phenylaziridine With manganese In N,N-dimethyl acetamide at 23℃; Inert atmosphere; Glovebox; Stage #2: With (1,2-dimethoxyethane)dichloronickel(II); 2,6-bis(pyrazole)pyridine In N,N-dimethyl acetamide at 23℃; for 18h; Inert atmosphere; Sealed tube;
55%	With manganese; (1,2-dimethoxyethane)dichloronickel(II); 2,6-bis(pyrazole)pyridine In N,N-dimethyl acetamide at 20℃; for 18h; Sealed tube; Inert atmosphere;

Reference： [1]Woods, Brian P.; Orlandi, Manuel; Huang, Chung-Yang; Sigman, Matthew S.; Doyle, Abigail G. [Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5688 - 5691]
[2]Woods, Brian P.; Orlandi, Manuel; Huang, Chung-Yang Dennis; Sigman, Matthew S.; Doyle, Abigail G. [Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7744 - 7745]

27
[ 408492-28-4 ]
N-trimethylsilyl N-(4-methoxybenzyl)-N-methylamine [ No CAS ]
[ 104-88-1 ]
1-(4-chlorophenyl)-N-(4-methoxybenzyl)-N-methyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: N-trimethylsilyl N-(4-methoxybenzyl)-N-methylamine; 4-chlorobenzaldehyde With t-butyldimethylsiyl triflate In 1,4-dioxane for 0.05h; Inert atmosphere; Glovebox; Stage #2: 2-(3-iodo-phenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane With nickel(II) bromide dimethoxyethane; 2,6-bis(pyrazole)pyridine; zinc In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Heinz, Christoph; Lutz, J. Patrick; Simmons, Eric M.; Miller, Michael M.; Ewing, William R.; Doyle, Abigail G. [Journal of the American Chemical Society, 2018, vol. 140, # 6, p. 2292 - 2300]

28
[ 408492-28-4 ]
[ 24395-14-0 ]
C₂₇H₃₂BNO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With manganese; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole; sodium iodide In tetrahydrofuran at -10℃; for 72h; Sealed tube; Inert atmosphere; enantioselective reaction;

Reference： [1]Woods, Brian P.; Orlandi, Manuel; Huang, Chung-Yang Dennis; Sigman, Matthew S.; Doyle, Abigail G. [Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7744 - 7745]

29
[ 408492-28-4 ]
[ 1197-22-4 ]
C₁₃H₁₂INO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium phosphate; tetrakis(actonitrile)copper(I) hexafluorophosphate In acetonitrile at 20℃;

Reference： [1]Vantourout, Julien C.; Li, Ling; Bendito-Moll, Enrique; Chabbra, Sonia; Arrington, Kenneth; Bode, Bela E.; Isidro-Llobet, Albert; Kowalski, John A.; Nilson, Mark G.; Wheelhouse, Katherine M. P.; Woodard, John L.; Xie, Shiping; Leitch, David C.; Watson, Allan J. B. [ACS Catalysis, 2018, vol. 8, # 10, p. 9560 - 9566]

30
[ 408492-28-4 ]
[ 1942-45-6 ]
(Z)-2-(3-(5-iodooct-4-en-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
(E)-2-(3-(5-iodooct-4-en-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 62% 2: 22%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 50℃; for 12h; Glovebox; Sealed tube;

Reference： [1]Takahashi, Toshifumi; Kuroda, Daiki; Kuwano, Toru; Yoshida, Yuji; Kurahashi, Takuya; Matsubara, Seijiro [Chemical Communications, 2018, vol. 54, # 90, p. 12750 - 12753]

31
[ 408492-28-4 ]
α-cumyl bromodifluoromethanesulfenate [ No CAS ]
(bromodifluoromethyl)(3-iodophenyl)thioether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With [(1,2-bis(diphenylphosphino)ethane)CuCl]; sodium t-butanolate In toluene at 50℃; for 2h; Inert atmosphere; Schlenk technique;

Reference： [1]Wu, Jiang; Zhao, Qunchao; Wilson, Thomas C.; Verhoog, Stefan; Lu, Long; Gouverneur, Véronique; Shen, Qilong [Angewandte Chemie - International Edition, 2019, vol. 58, # 8, p. 2413 - 2417][Angew. Chem., 2019, vol. 131, # 8, p. 2435 - 2439,5]

32
[ 408492-28-4 ]
[ 201230-82-2 ]
[ 99591-51-2 ]
3-methyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc diacetate In tetrahydrofuran; hexane at 80℃; for 16h; Autoclave; Inert atmosphere;

Reference： [1]Chen, Bo; Wu, Xiao-Feng [Organic Letters, 2019, vol. 21, # 18, p. 7624 - 7629]

33
[ 408492-28-4 ]
[ 1520-31-6 ]
dimethyl-oxo-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]imino-λ6-sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With (1,2-dimethoxyethane)dichloronickel(II); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 29℃; for 16h; Irradiation; chemoselective reaction;	General Procedure General procedure: Ir[dF(CF3)ppy]2(dtbpy))PF6(5.6 mg, 4.99 µmol) was added to a stirred solution of aryl iodide (1.00 mmol), iminodimethyl-λ6-sulfanone (102 mg, 1.10 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (20 mg, 0.07 mmol), TEA (0.279 mL, 2.00 mmol) and NiCl2(glyme) (11 mg, 0.05 mmol) in acetonitrile (5.6 mL). The resulting mixture was irradiated with a blue LED (450 nm, Penn Optical Photoreactor m1) and stirred at 29 °C for 16 hours. The reaction mixture was quenched with saturated aqueous NaHCO3(2 mL) and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure.The resulting residue was purified by flash silica chromatography to afford the corresponding products.

Reference： [1]Hande, Sudhir; Mfuh, Adelphe; Throner, Scott; Wu, Ye; Ye, Qing; Zheng, XiaoLan [Tetrahedron Letters, 2019, vol. 60, # 41]

34
[ 408492-28-4 ]
[ 1945-84-2 ]
[ 107737-89-3 ]
4'-(2-hydroxyethanesulfonyl)-3-(pyridin-2-ylethynyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Patent: JP2019/182779,2019,A .Location in patent: Paragraph 0316-0317

35
[ 408492-28-4 ]
trans-4'-(2-hydroxyethanesulfonyl)-4-propyl-5-(2-(pyridin-2-yl)cyclopropyl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 20 °C 1.2: 12 h / 100 °C 2.1: formic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane / 1,4-dioxane / 80 °C 3.1: trifluoroacetic acid; dimethyl zinc(II) / dichloromethane / 2.5 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: JAPAN HEALTH SCIENCES FOUNDATION - JP2019/182779, 2019, A

36
[ 408492-28-4 ]
4'-(2-hydroxyethanesulfonyl)-3-(pyridin-2-ylethyl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 20 °C 1.2: 12 h / 100 °C 2.1: hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr

Reference： [1]Current Patent Assignee: JAPAN HEALTH SCIENCES FOUNDATION - JP2019/182779, 2019, A

37
[ 408492-28-4 ]
(E)-4'-(2-hydroxyethanesulfonyl)-3-(pyridin-2-yl-2-vinyl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 20 °C 1.2: 12 h / 100 °C 2.1: formic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane / 1,4-dioxane / 15 h / 80 °C

Reference： [1]Current Patent Assignee: JAPAN HEALTH SCIENCES FOUNDATION - JP2019/182779, 2019, A

38
[ 408492-28-4 ]
(Z)-4'-(2-hydroxyethanesulfonyl)-3-(pyridin-2-yl-2-vinyl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 20 °C 1.2: 12 h / 100 °C 2.1: formic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane / 1,4-dioxane / 80 °C

Reference： [1]Current Patent Assignee: JAPAN HEALTH SCIENCES FOUNDATION - JP2019/182779, 2019, A

39
[ 408492-28-4 ]
cis-4'-(2-hydroxyethanesulfonyl)-3-(2-(pyridin-2-yl)cyclopropyl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 12 h / 20 °C 1.2: 12 h / 100 °C 2.1: formic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane / 1,4-dioxane / 15 h / 80 °C 3.1: trifluoroacetic acid; dimethyl zinc(II) / dichloromethane / 2.5 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: JAPAN HEALTH SCIENCES FOUNDATION - JP2019/182779, 2019, A

40
phenylene-1,3-diammonium sulfate [ No CAS ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium nitrite; potassium iodide; hydrogenchloride / water / 2 h / 0 - 20 °C 2: n-butyllithium; Triisopropyl borate / tetrahydrofuran; diethyl ether / 21 h / -78 - 20 °C 3: calcium sulfate / toluene / 3.5 h / Reflux

Reference： [1]Current Patent Assignee: JAPAN HEALTH SCIENCES FOUNDATION - JP2019/182779, 2019, A

41
[ 626-00-6 ]
[ 408492-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-butyllithium; Triisopropyl borate / tetrahydrofuran; diethyl ether / 21 h / -78 - 20 °C 2: calcium sulfate / toluene / 3.5 h / Reflux

Reference： [1]Current Patent Assignee: JAPAN HEALTH SCIENCES FOUNDATION - JP2019/182779, 2019, A

42
[ 408492-28-4 ]
C₁₈H₂₆BClO₂Zr [ No CAS ]
4,4,5,5-tetramethyl-2-(3-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)phenyl)-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88 mg	With 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide In tetrahydrofuran at 25 - 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; chemoselective reaction;

Reference： [1]Bai, Songlin; Gao, Yadong; Jiang, Chao; Qi, Xiangbing; Yang, Chao [Journal of the American Chemical Society, 2020, vol. 142, # 26, p. 11506 - 11513]

43
[ 408492-28-4 ]
[ 100-42-5 ]
[ 201230-82-2 ]
[ 73183-34-3 ]
2-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With bis(η3-allyl-μ-chloropalladium(II)); chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I); 1,3-bis-(diphenylphosphino)propane; sodium t-butanolate In toluene at 80℃; for 12h; Autoclave;

Reference： [1]Wu, Fu-Peng; Wu, Xiao-Feng; Xu, Jian-Xing; Yuan, Yang [Angewandte Chemie - International Edition, 2020, vol. 59, # 39, p. 17055 - 17061][Angew. Chem., 2020, vol. 132, # 39, p. 17203 - 17209,7]

44
[ 408492-28-4 ]
[ 1239085-99-4 ]
C₂₃H₂₇BO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Börjesson, Marino; Duan, Yaya; Janssen-Müller, Daniel; Martin, Ruben; Sahoo, Basudev; Wang, Xueqiang [Journal of the American Chemical Society, 2020, vol. 142, # 38, p. 16234 - 16239]

45
[ 408492-28-4 ]
3-((3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)phenyl)ethynyl)-3-(difluoromethyl)-1-methylpyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2 h / 70 °C / Microwave irradiation 2: caesium carbonate; chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation / water; 1,4-dioxane / 1 h / 110 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; ZHAN SEN PHARMACOLOGICAL CO LTD - WO2020/239999, 2020, A1

46
[ 408492-28-4 ]
(R)-3-((3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)phenyl)ethynyl)-3-(difluoromethyl)-1-methylpyrrolidin-2-one [ No CAS ]
(S)-3-((3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)phenyl)ethynyl)-3-(difluoromethyl)-1-methylpyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2 h / 70 °C / Microwave irradiation 2: caesium carbonate; chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation / water; 1,4-dioxane / 1 h / 110 °C 3: carbon dioxide / ethanol; water / Resolution of racemate; Supercritical conditions

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; ZHAN SEN PHARMACOLOGICAL CO LTD - WO2020/239999, 2020, A1

47
[ 408492-28-4 ]
(R)-2-ethynyl-2-hydroxy-5,5-dimethylcyclopentan-1-one [ No CAS ]
(R)-2-hydroxy-5,5-dimethyl-2-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)cyclopentan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 100℃; for 0.5h; Inert atmosphere; Sealed tube;	Intermediate 4: (R)-3-Hydroxy-1-methyl-3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)ethynyl)pyrrolidin-2-one General procedure: 2-(3-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.22 g, 32.6 mmol), (R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one (5.00 g, 35.9 mmol), and diethylamine (33.7 mL, 326 mmol) were suspended in degassed DMF (217 mL). Nitrogen gas was then bubbled through the reaction for 5 min. Copper(I) Iodide (1.24 g, 6.52 mmol), bis(triphenylphosphine)palladium(II) dichloride (2.29 g, 3.26 mmol) andtriphenylphosphine (1.71 g, 6.52 mmol) were added to the mixture. The reaction was sealed and was then heated to 100 °C for 30 min. The resulting mixture was then passed through a plug of diatomaceous earth, such as Celite, washed with DMF, and concentrated under reduced pressure. The resulting residue was purified by FCC (0% hexanes over 3 min, 25%-100% EtOAc/hexanes over 25 min, 100% EtOAc over 3 min) to give (R)-3-hydroxy-1-methyl-3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)ethynyl)pyrrolidin-2-one (7.50 g, 67.5%) as an off-white solid. MS (ESI): mass calcd. For C19H24BNO4, 341.18; m/z found, 342.1 [M+H]+.1H NMR (400 MHz, DMSO- d6) d 7.70- 7.68 (m, 1H), 7.66 (dt, J = 7.4, 1.3 Hz, 1H), 7.54 (dt, J = 7.8, 1.5 Hz, 1H), 7.41 (td, J = 7.6, 0.7 Hz, 1H), 6.44 (s, 1H), 3.37- 3.32 (m, 2H), 2.80 (s, 3H), 2.46- 2.37 (m, 1H), 2.20- 2.02 (m, 1H), 1.30 (s, 12H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; ZHAN SEN PHARMACOLOGICAL CO LTD - WO2020/239999, 2020, A1 Location in patent: Page/Page column 130; 131; 207

48
[ 408492-28-4 ]
(S)-2-ethynyl-2-hydroxy-5,5-dimethylcyclopentan-1-one [ No CAS ]
(S)-2-hydroxy-5,5-dimethyl-2-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)cyclopentan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 100℃; for 0.5h; Inert atmosphere; Sealed tube;	Intermediate 4: (R)-3-Hydroxy-1-methyl-3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)ethynyl)pyrrolidin-2-one General procedure: 2-(3-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.22 g, 32.6 mmol), (R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one (5.00 g, 35.9 mmol), and diethylamine (33.7 mL, 326 mmol) were suspended in degassed DMF (217 mL). Nitrogen gas was then bubbled through the reaction for 5 min. Copper(I) Iodide (1.24 g, 6.52 mmol), bis(triphenylphosphine)palladium(II) dichloride (2.29 g, 3.26 mmol) andtriphenylphosphine (1.71 g, 6.52 mmol) were added to the mixture. The reaction was sealed and was then heated to 100 °C for 30 min. The resulting mixture was then passed through a plug of diatomaceous earth, such as Celite, washed with DMF, and concentrated under reduced pressure. The resulting residue was purified by FCC (0% hexanes over 3 min, 25%-100% EtOAc/hexanes over 25 min, 100% EtOAc over 3 min) to give (R)-3-hydroxy-1-methyl-3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)ethynyl)pyrrolidin-2-one (7.50 g, 67.5%) as an off-white solid. MS (ESI): mass calcd. For C19H24BNO4, 341.18; m/z found, 342.1 [M+H]+.1H NMR (400 MHz, DMSO- d6) d 7.70- 7.68 (m, 1H), 7.66 (dt, J = 7.4, 1.3 Hz, 1H), 7.54 (dt, J = 7.8, 1.5 Hz, 1H), 7.41 (td, J = 7.6, 0.7 Hz, 1H), 6.44 (s, 1H), 3.37- 3.32 (m, 2H), 2.80 (s, 3H), 2.46- 2.37 (m, 1H), 2.20- 2.02 (m, 1H), 1.30 (s, 12H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; ZHAN SEN PHARMACOLOGICAL CO LTD - WO2020/239999, 2020, A1 Location in patent: Page/Page column 130; 131; 207; 208

49
[ 408492-28-4 ]
3-(difluoromethyl)-3-ethynyl-1-methylpyrrolidin-2-one [ No CAS ]
3-(difluoromethyl)-1-methyl-3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 70℃; for 2h; Microwave irradiation;	E Step E: 3-(Difluoromethyl)-1-methyl-3-((3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)phenyl)ethynyl)pyrrolidin-2-one 2-(3-Iodophenyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (280 mg, 0.85 mmol), 3-(difluoromethyl)-3-ethynyl-1- methylpyrrolidin-2-one (130 mg, 0.75 mmol), TEA (2.5 mL), and DMF (2.5 mL) were added to a microwave tube. The mixture was purged with Ar for 5 min and then treated with Pd(PPh3)2Cl2 (53 mg, 0.076 mmol) and CuI (29 mg, 0.15 mmol). The mixture was purged with Ar for another 5 min and then stirred at 70 °C for 2 h before cooling to rt. The resulting mixture was poured into aqueous LiCl (4% in water, 20 mL) and extracted with ethyl acetate (20 mL x 4). The combined organic extracts were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness to afford a mixture of 3-(difluoromethyl)-1-methyl-3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl)ethynyl)pyrrolidin-2-one and (3-((3-(difluoromethyl)-1-methyl-2-oxopyrrolidin-3- yl)ethynyl)phenyl)boronic acid (360 mg) as a brown oil which was used without further purification. MS (ESI): mass calcd. for C20H24BF2NO3375.2 m/z found 376.2 [M+H]+.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; ZHAN SEN PHARMACOLOGICAL CO LTD - WO2020/239999, 2020, A1 Location in patent: Page/Page column 251; 252

50
[ 408492-28-4 ]
[ 14850-23-8 ]
4,4,5,5-tetramethyl-2-(3-octylphenyl)-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With nickel(II) bromide dimethoxyethane; potassium fluoride; Triethoxysilane; 2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole In N,N-dimethyl-formamide for 24h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]He, Yuli; Han, Bo; Zhu, Shaolin [Organometallics, 2021, vol. 40, # 14, p. 2253 - 2264]

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P222	Do not allow contact with air.
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere