Premium
Unexpected regioselectivity in the palladium‐catalyzed reaction of silacyclobutanes with aryl iodides
Author(s) -
Tanaka Yoshifumi,
Nishigaki Atsushi,
Kimura Yutaka,
Yamashita Masakazu
Publication year - 2001
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.206
Subject(s) - regioselectivity , chemistry , aryl , palladium , catalysis , medicinal chemistry , silanes , organic chemistry , ring (chemistry) , silane , alkyl
The reaction of aryl iodides with 1,1‐diphenyl‐silacyclobutane in the presence of a catalytic amount of Pd(PPh 3 ) 4 affords unexpected ring‐opening adducts, 1‐ and 2‐propenyl(triaryl)‐silanes, in good yields. On the other hand, the PdCl 2 (PhCN) 2 ‐catalyzed reaction of 1,1‐diphenylsilacyclobutanes with aryl halides gives unexpected products, triarylsilanols, after hydrolysis in moderate yields. The catalysis involves the reaction of aryl–palladium intermediates with silacyclobutanes along with regioselective aryl–silicon bond formation. Copyright © 2001 John Wiley & Sons, Ltd.