TY - JOUR
T1 - Iridium-catalyzed (Z)-trialkylsilylation of terminal olefins
AU - Lu, Biao
AU - Falck, J. R.
PY - 2010/3/5
Y1 - 2010/3/5
N2 - (Chemical equation presented) A complex of commercial [Ir(OMe)(cod)] 2 and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrative silylation of terminal alkenes, but not 1,2-disubstituted alkenes, with triethylsilane or benzyldimethylsilane in THF at 40 °C. Yields and Z-stereoselectivity were significantly improved by 2-norbornene, in contrast with other sacrificial alkenes. The reaction is compatible with many functional groups including epoxides, ketones, amides, alcohols, esters, halides, ketals, and silanes. α, β-Unsaturated esters were unreactive. The reaction probably proceeds through a Heck-type mechanism.
AB - (Chemical equation presented) A complex of commercial [Ir(OMe)(cod)] 2 and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrative silylation of terminal alkenes, but not 1,2-disubstituted alkenes, with triethylsilane or benzyldimethylsilane in THF at 40 °C. Yields and Z-stereoselectivity were significantly improved by 2-norbornene, in contrast with other sacrificial alkenes. The reaction is compatible with many functional groups including epoxides, ketones, amides, alcohols, esters, halides, ketals, and silanes. α, β-Unsaturated esters were unreactive. The reaction probably proceeds through a Heck-type mechanism.
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U2 - 10.1021/jo902678p
DO - 10.1021/jo902678p
M3 - Article
C2 - 20136153
AN - SCOPUS:77949279284
SN - 0022-3263
VL - 75
SP - 1701
EP - 1705
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -