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4.4.7.2.2.2 Base-Catalyzed Silaboration

DOI: 10.1055/sos-SD-104-00395

Delvos, L. B.; Oestreich, M.Science of Synthesis Knowledge Updates, (2017195.

Styrene derivatives 76 react in the presence of potassium tert-butoxide as catalyst with silylboronic ester 19 to generate 1,2-difunctionalized alkanes 77 as single regioisomers (Scheme 36).[‌67‌] The reaction proceeds well for electron-rich arenes but fails in the case of a trifluoromethyl-functionalized aryl group. 1,1-Disubstitution is tolerated, and unsymmetrically 1,2-disubstituted acceptors yield predominantly the anti-configured adducts independent of the double-bond geometry of the starting material. However, symmetric E-stilbene (76, R1 = R3 = Ph; R2 = H) is converted into the corresponding alkane isomer 77 (R1 = R3 = Ph; R2 = H) with almost no selectivity. Generally, the yields are superior to the transition-metal-catalyzed variant, but only styrenes have been shown to react so far.

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