[ CAS No. 171364-84-4 ] {[proInfo.proName]}

Name: 171364-84-4|4,4,5,5-Tetramethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborolane|95%
Brand: Ambeed
SKU: A135325
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Quality Control of [ 171364-84-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 171364-84-4 ]

SDS Specification

Alternatived Products of [ 171364-84-4 ]

Product Details of [ 171364-84-4 ]

CAS No. :	171364-84-4	MDL No. :	MFCD22414456
Formula :	C₁₅H₂₃BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MUSASZSRBLWJQA-UHFFFAOYSA-N
M.W :	246.15	Pubchem ID :	10847983
Synonyms :

Calculated chemistry of [ 171364-84-4 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.6
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	77.82
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.0
Log Po/w (WLOGP) :	2.91
Log Po/w (MLOGP) :	2.54
Log Po/w (SILICOS-IT) :	3.33
Consensus Log Po/w :	2.56

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.07
Solubility :	0.0211 mg/ml ; 0.0000857 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.09
Solubility :	0.02 mg/ml ; 0.0000813 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.16
Solubility :	0.00169 mg/ml ; 0.00000685 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.15

Safety of [ 171364-84-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 171364-84-4 ]

* 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.

Downstream synthetic route of [ 171364-84-4 ]

[ 171364-84-4 ] Synthesis Path-Downstream 1~50

1
[ 76-09-5 ]
[ 576-83-0 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 2,4,6-trimethylphenyl bromide With magnesium In tetrahydrofuran Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Stage #3: 2,3-dimethyl-2,3-butane diol In toluene Heating; Further stages.;

Reference： [1]Wong, Ken-Tsung; Chien, Yuh-Yih; Liao, Yuan-Li; Lin, Chang-Chih; Chou, Meng-Yen; Leung, Man-Kit [Journal of Organic Chemistry, 2002, vol. 67, # 3, p. 1041 - 1044]

2
[ 576-83-0 ]
[ 25015-63-8 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In 1,4-dioxane at 110℃; for 4h;
67%	Stage #1: 2,4,6-trimethylphenyl bromide; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(trifluoromethane)sulfonimide lithium In tetrahydrofuran at 20℃; Electrochemical reaction; Stage #2: With sulfuric acid at 0℃; Further stages.;
25%	With palladium diacetate; triethylamine; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran; 1,4-dioxane at 100℃; for 20h;

Reference： [1]Billingsley, Kelvin L.; Buchwald, Stephen L. [Journal of Organic Chemistry, 2008, vol. 73, # 14, p. 5589 - 5591]
[2]Laza, Carine; Dunach, Elisabet [Advanced Synthesis and Catalysis, 2003, vol. 345, # 5, p. 580 - 583]
[3]Broutin, Pierre-Emmanuel; Cerna, Igor; Campaniello, Maria; Leroux, Frederic; Colobert, Francoise [Organic Letters, 2004, vol. 6, # 24, p. 4419 - 4422]

3
[ 1160000-82-7 ]
[ 171364-84-4 ]
[ 1160000-89-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In N,N-dimethyl-formamide; toluene at 120℃; for 4.5h; Inert atmosphere;

Reference： [1]Suzuki, Shuichi; Takeda, Takuma; Kuratsu, Masato; Kozaki, Masatoshi; Sato, Kazunobu; Shiomi, Daisuke; Takui, Takeji; Okada, Keiji [Organic Letters, 2009, vol. 11, # 13, p. 2816 - 2818]

4
[ 576-83-0 ]
[ 73183-34-3 ]
[ 94647-81-1 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With copper(l) iodide; tributylphosphine; potassium <i>tert</i>-butylate In tetrahydrofuran byproducts: KBr, (CH3)3C6H3; react. of (B(OC(CH3)2)2)2 (1.5 equiv.), 2,4,6-Me3C6H2Br (1 equiv.), CuI (10 mol%), nBu3P (13 mol%) and KOtBu (1.5 equiv.) at room temp.;

Reference： [1]Kleeberg, Christian; Dang, Li; Lin, Zhenyang; Marder, Todd B. [Angewandte Chemie - International Edition, 2009, vol. 48, p. 5350 - 5354][Angew. Chem., Int. Ed., 2009, vol. 121, p. 5454 - 5458]

5
[ 576-83-0 ]
[ 73183-34-3 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With [(Pd(μ-Cl)(κ(2)-P,C-P(OC6H2-2,4-tBu2)(OC6H3-2,4-tBu2)2))2]; 4- (9-anthryl) -3-(tert-butyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole; potassium acetate In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere;
94%	With P(p-CH₃OC₆H₄)3; palladium diacetate; caesium carbonate In ethyl acetate at 80℃; for 8h; Sealed tube;
93%	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium acetate In water at 20℃; for 9h; Inert atmosphere;

88%	With DPEPhos; sodium acetate; bis(dibenzylideneacetone)-palladium⁽⁰⁾ for 12h; Heating;
71%	With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In neat (no solvent) at 110℃; for 24h;	3.1. Miyaura borylation General procedure: Under atmospheric conditions, a 10-mL screwcap vial equipped with a magnetic stir bar was charged with Pd source (0.01 mmol, 0.02 equiv), base (0.6 mmol, 1.2 equiv), bis(pinacolato)diboron (0.525 mmol, 1.05 equiv) and aryl halide (0.5 mmol, 1 equiv). The reaction vial was transferred to a preheated oil bath. The reaction was stirred at 110 °C for the desired time to give a grey mixture. The reaction mixture was extracted with 10 mL of ethyl acetate, washed with water (2 × 15 mL), brine (10 mL), and dried over Na2SO4. The solvent was evaporated in vacuo to afford the crude product. The product yield was determined by GC-FID based on integration relative to hexamethylbenzene as an internal standard. The residue was purified by column chromatography on silica gel (eluting with 5:95 ethyl acetate in hexane) to give pure aryl boronic ester.
69%	With copper(l) iodide; tributyl-amine; potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃;
41%	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In acetonitrile at 25℃; for 8h; Irradiation; Inert atmosphere;
40%	With potassium tetrachloropalladate(II); potassium acetate at 70℃; for 6h; Inert atmosphere;
40%	With C₂₆H₂₅Cl₂FeN₂PPd; potassium acetate In isopropyl alcohol at 85℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; Patel, Nitinchandra D.; Yee, Nathan K.; Senanayake, Chris H. [Organic Letters, 2011, vol. 13, # 6, p. 1366 - 1369]
[2]Kuwano, Ryoichi; Lee, Eunhyung; Won, Sungyong [Organic Letters, 2021, vol. 23, # 24, p. 9649 - 9653]
[3]Lipshutz, Bruce H.; Moser, Ralph; Voigtritter, Karl R. [Israel Journal of Chemistry, 2010, vol. 50, # 5-6, p. 691 - 695]
[4]Dzhevakov, Pavel B.; Topchiy, Maxim A.; Zharkova, Daria A.; Morozov, Oleg S.; Asachenko, Andrey F.; Nechaev, Mikhail S. [Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983]
[5]Boontiem, Phongsakorn; Kiatisevi, Supavadee [Inorganica Chimica Acta, 2020, vol. 506]
[6]Kleeberg, Christian; Dang, Li; Lin, Zhenyang; Marder, Todd B. [Angewandte Chemie - International Edition, 2009, vol. 48, p. 5350 - 5354][Angew. Chem., Int. Ed., 2009, vol. 121, p. 5454 - 5458]
[7]Zhao, Jia-Hui; Zhou, Zhao-Zhao; Zhang, Yue; Su, Xuan; Chen, Xi-Meng; Liang, Yong-Min [Organic and Biomolecular Chemistry, 2020, vol. 18, # 23, p. 4390 - 4394]
[8]Location in patent: experimental part Bej, Ansuman; Srimani, Dipankar; Sarkar, Amitabha [Green Chemistry, 2012, vol. 14, # 3, p. 661 - 667]
[9]Škoch, Karel; Schulz, Jiří; Císařová, Ivana; Štěpnička, Petr [Organometallics, 2019, vol. 38, # 15, p. 3060 - 3073]

6
[ 73183-34-3 ]
[ 108-67-8 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With Pt(N,N′-dicyclohexylimidazol-2-ylidene)(divinyltetramethylsiloxane) at 120℃; for 20h; Inert atmosphere; Sealed tube;
41%	With tert-butyl peroxide; K₂CO₃ In benzene under air, (t-BuO)2 2.0 equiv., K2CO3 2.0 equiv., Fe2O3 0.2 equiv.; 80 °C, 5 d;
41 %Chromat.	With iron(III) oxide; di-tert-butyl peroxide; potassium carbonate at 80℃;

72 %Chromat.

With C₃₅H₅₀N₂OPtSi₂ at 120℃; for 20h;

Reference： [1]Furukawa, Takayuki; Tobisu, Mamoru; Chatani, Naoto [Journal of the American Chemical Society, 2015, vol. 137, # 38, p. 12211 - 12214]
[2]Yan, Guobing; Jiang, Yubo; Kuang, Chunxiang; Wang, Shuai; Liu, Haichao; Zhang, Yan; Wang, Jianbo [Chemical Communications, 2010, vol. 46, # 18, p. 3170 - 3172]
[3]Location in patent: experimental part Yan, Guobing; Jiang, Yubo; Kuang, Chunxiang; Wang, Shuai; Liu, Haichao; Zhang, Yan; Wang, Jianbo [Chemical Communications, 2010, vol. 46, # 18, p. 3170 - 3172]
[4]Furukawa, Takayuki; Tobisu, Mamoru; Chatani, Naoto [Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 332 - 342]

7
[ 75732-01-3 ]
[ 73183-34-3 ]
2-(2,4,6-trimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 235 - 238
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 235 - 238

8
[ 171364-84-4 ]
[ 626232-27-7 ]
[ 3360-56-3 ]

Yield	Reaction Conditions	Operation in experiment
49%	With oxygen; copper diacetate In dimethyl sulfoxide at 60℃; for 16h;

Reference： [1]Khan, Bilal A.; Buba, Annette E.; Goossen, Lukas J. [Chemistry - A European Journal, 2012, vol. 18, # 6, p. 1577 - 1581]

9
[ 156-60-5 ]
[ 171364-84-4 ]
[ 18684-99-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium phosphate; [Rh(OH)(cod)]2; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 100℃; for 5h; Schlenk technique; Inert atmosphere;
	With potassium phosphate; [Rh(OH)(cod)]2; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 100℃;

Reference： [1]Matsuda, Takanori; Suzuki, Kentaro; Miura, Norio [Advanced Synthesis and Catalysis, 2013, vol. 355, # 17, p. 3396 - 3400]
[2]Kanazawa, Junichiro; Miyamoto, Kazunori; Takagi, Taisei; Uchiyama, Masanobu; Watanabe, Yuichiro [Organic Letters, 2020, vol. 22, # 9, p. 3469 - 3473]

10
[ 4028-63-1 ]
[ 73183-34-3 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: bis(pinacol)diborane With diethylzinc; sodium t-butanolate In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Schlenk technique; Glovebox; Inert atmosphere; Stage #2: iodomesitylene In tetrahydrofuran; hexane at 20 - 120℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube;
53%	With p-phenylpyridine; potassium methanolate In tert-butyl methyl ether at 85℃; for 12h; Sealed tube;
50%	With tetrabutylammomium bromide; C₅₅H₄₆N₄O₄W; potassium carbonate In acetonitrile at 20℃; for 12h; Irradiation;

49%	With lithium tert-butoxide In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique;
40%	With pyridine; C₅₀H₄₄CuN₄OP₂⁽¹⁺⁾*F₆P^(1-); N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;
25%	With potassium methanolate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; zinc dibromide In tert-butyl methyl ether at 50℃; Inert atmosphere; Glovebox; Schlenk technique; Green chemistry;
17.4 mg	Stage #1: bis(pinacol)diborane With potassium ethoxide; C₄₀H₆₂N₄Zn₂ In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: iodomesitylene In tetrahydrofuran at 75℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;

Reference： [1]Nagashima, Yuki; Takita, Ryo; Yoshida, Kengo; Hirano, Keiichi; Uchiyama, Masanobu [Journal of the American Chemical Society, 2013, vol. 135, # 50, p. 18730 - 18733]
[2]Zhang, Li; Jiao, Lei [Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610]
[3]Chan, Kaai-Tung; Che, Chi-Ming; Du, Lili; Liu, Yungen; Phillips, David Lee; To, Wai-Pong; Tong, Glenna So Ming; Wu, Liang-Liang; Yu, Daohong [Chemical Science, 2020, vol. 11, # 25, p. 6370 - 6382]
[4]Cid, M. B.; Díaz, Cristina; Franco, Mario; Lamsabhi, Al Mokhtar; Sainz, Raquel; Tortosa, Mariola [Catalysis science and technology, 2021, vol. 11, # 10, p. 3501 - 3513]
[5]Nitelet, Antoine; Thevenet, Damien; Schiavi, Bruno; Hardouin, Christophe; Fournier, Jean; Tamion, Rodolphe; Pannecoucke, Xavier; Jubault, Philippe; Poisson, Thomas [Chemistry - A European Journal, 2019, vol. 25, # 13, p. 3262 - 3266]
[6]Bose, Shubhankar Kumar; Marder, Todd B. [Organic Letters, 2014, vol. 16, # 17, p. 4562 - 4565]
[7]Li, Yafei; Dang, Yan; Li, Dawei; Pan, Huifen; Zhang, Liang; Wang, Li; Cao, Zhu; Li, Yahong [Organometallics, 2021, vol. 40, # 4, p. 482 - 489]

11
[ 106-38-7 ]
[ 171364-84-4 ]
[ 3976-37-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium hydroxide In neat (no solvent) at 110℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Asachenko, Andrey F.; Sorochkina, Kristina R.; Dzhevakov, Pavel B.; Topchiy, Maxim A.; Nechaev, Mikhail S. [Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3553 - 3557]

12
[ 76-09-5 ]
[ 5980-97-2 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium sulfate In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;
	In diethyl ether at 20℃; for 18h; Inert atmosphere;

Reference： [1]Asachenko, Andrey F.; Sorochkina, Kristina R.; Dzhevakov, Pavel B.; Topchiy, Maxim A.; Nechaev, Mikhail S. [Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3553 - 3557]
[2]Ling, Liang; He, Yuan; Zhang, Xue; Luo, Meiming; Zeng, Xiaoming [Angewandte Chemie - International Edition, 2019, vol. 58, # 20, p. 6554 - 6558][Angew. Chem., 2019, vol. 131, # 20, p. 6626 - 6630,5]

13
[ 1804049-23-7 ]
[ 73183-34-3 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
34%	In methanol at 50℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Miralles; Romero; Fernández; Muñiz [Chemical Communications, 2015, vol. 51, # 74, p. 14068 - 14071]

14
[ 1310694-10-0 ]
[ 73183-34-3 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; potassium <i>tert</i>-butylate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In 2-ethoxy-ethanol; toluene at 50℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Hu, Jiefeng; Sun, Heqing; Cai, Wangshui; Pu, Xinghui; Zhang, Yemin; Shi, Zhuangzhi [Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 14 - 24]

15
[ 353752-15-5 ]
[ 171364-84-4 ]
[ 1883685-87-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 24h;

Reference： [1]Zhang, Gang; Lami, Vincent; Rominger, Frank; Vaynzof, Yana; Mastalerz, Michael [Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3977 - 3981][Angew. Chem., 2016, vol. 128, # 12, p. 4045 - 4049,5]

16
[ 58047-42-0 ]
2-(2,4,6-trimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]
C₂₉H₃₀BNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		The reactions were set up and run in a nitrogen-purged glovebox. 4-Bromo-4' ,4"- dimethyltriphenylamine (6.0 g, 17 mmol from eNovation Chemicals) was dissolved in 60 mL diethyl ether and cooled in a freezer set to -40 C. The solution was removed from the freezer and n-butyllithium (7.2 mL of a 2.5M solution in hexanes) was slowly added. The resulting mixture was stirred for four hours as the temperature was allowed to rise to room temperature. The resulting mixture was placed in a freezer at -40 C. In a separate jar, 2,4,6- trimethylphenylboronic acid pinacol ester (4.6 g, 19 mmol from AKSci) was dissolved in 30 mL diethyl ether. After cooling the second solution in the freezer, the aryllithium suspension was slowly added to the boronic ester solution. The resulting mixture was stirred overnight at room temperature. The resulting mixture was removed from the glovebox and poured into 1M HC1. After mixing for about 5 minutes, the resulting yellow organic layer was isolated and brought back into the glovebox. Solvent was removed in vacuo and the residue was purified by flash chromatography using a gradient of hexanes and ethyl acetate on an ISCO Combiflash. Solvent was removed in vacuo from the product to yield 3.6 g (50% yield). H NMR (500 MHz, CD2C12): delta 7.52 - 7.45 (m, 2H), 7.11 (d, J = 8.1 Hz, 4H), 7.02 (d, J = 8.1 Hz, 4H), 6.89 - 6.85 (m, 2H), 6.83 (s, 2H), 5.70 (s, 1H), 2.32 (s, 6H), 2.28 (s, 3H), 2.19 (s, 6H). ppm. 13C NMR (126 MHz, CD2C12): delta 152.0, 145.1, 139.5, 138.2, 136.9, 134.4, 130.6, 127.6, 126.3, 119.7, 22.4, 21.5, 21.2 ppm. nB NMR (160 MHz, CD2C12): delta 47.5 ppm.

Reference： [1]Patent: WO2016/178827,2016,A1 .Location in patent: Page/Page column 27-28

17
[ 171364-84-4 ]
[ 210823-55-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 115℃; for 0.25h;

Reference： [1]Petersen, Ida Nymann; Kristensen, Jesper Langgaard; Herth, Matthias Manfred [European Journal of Organic Chemistry, 2017, vol. 2017, # 3, p. 453 - 458]

18
[ 4028-63-1 ]
[ 78782-17-9 ]
[ 171364-84-4 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium t-butanolate In tetrahydrofuran; toluene at 120℃; for 6h; Inert atmosphere; Sealed tube; chemoselective reaction;

Reference： [1]Lee, Yeosan; Baek, Seung-Yeol; Park, Jinyoung; Kim, Seoung-Tae; Tussupbayev, Samat; Kim, Jeongho; Baik, Mu-Hyun; Cho, Seung Hwan [Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 975 - 984]

19
[ 171364-84-4 ]
[ 2191374-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / diethyl ether / -78 - 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: benzene / 1 h / 20 - 80 °C / Inert atmosphere