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With C35H52N2OPtSi2; at 120℃; for 36h;Sealed tube; Inert atmosphere;
Pt(SIPr)(dvtms) (6.9 mg, 9.0 mol), B2pin2 (91 mg, 0.36 mmol), methyl 4-methylbenzoate (49mg, 0.30 mmol) and 1,3,5-triisopropylbenzene (0.10 mL) were added to a 10 mL-sample vial witha Teflon-sealed screwcap. The cap was applied to seal the vial under the flow of N2. The mixturewas stirred at 120 C for 20 h and the resulting mixture was filtered through a pad of silica gel(eluting with 7 mL of hexane/EtOAc = 5/1). The filtrate was concentrated in vacuo and purifiedby flash column chromatography over silica gel (eluting with hexane/AcOEt = 100/1 to 50/1) togive the target borylated product as a white solid (35 mg, 42%) and 26 mg of unreacted startingmaterial was recovered (52%). The recovered starting material was transferred to another vial forrepeating the borylation. Pt(SIPr)(dvtms) (4.9 mg, 6.4 mol), B2pin2 (51 mg, 0.20 mmol) and1,3,5-triisopropylbenzen (0.1 mL) were added. The mixture was stirred at 120 C for 16 h and theresulting mixture was filtered through a pad of silica gel (eluting with 7 mL of hexane/AcOEt =5/1). The filtrate was concentrated in vacuo and purified by flash column chromatography to givethe target borylated product (14 mg, 17% based on starting arene) and 7.9 mg of unreacted startingmaterial was recovered. As a result of two borylation, 59% of the target product was obtained and16% of unreacted starting was recovered.Rf 0.49 (hexane/EtOAc = 5/1). White solid (49 mg, 59%).
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