Premium
Metal‐Catalyzed Sequential Formation of Distant Bonds in Organic Molecules: Palladium‐Catalyzed Hydrosilylation/Cyclization of 1, n ‐Dienes by Chain Walking
Author(s) -
Kochi Takuya,
Ichinose Kazuya,
Shigekane Masayuki,
Hamasaki Taro,
Kakiuchi Fumitoshi
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201814558
Subject(s) - hydrosilylation , catalysis , palladium , cyclopentane , molecule , chemistry , diene , organic synthesis , metal , double bond , photochemistry , polymer chemistry , organic chemistry , natural rubber
Sequential formation of distant bonds in organic molecules was achieved for the palladium‐catalyzed hydrosilylation/cyclization of various 1, n ‐dienes by chain walking of the metal catalyst. The reaction was applicable to various 1, n ‐dienes, including a 1,13‐diene, to form a cyclopentane ring as well as a carbon–silicon bond at a remote site. The use of “nondissociative” chain walking provides a fascinating strategy in organic synthesis to functionalize distant parts of organic molecules, in a particular order, within a catalytic cycle by effectively moving the reactive center from a remote position.