TY - JOUR
T1 - Catalytic, Directed C-C Bond Functionalization of Styrenes
AU - Onodera, Shunsuke
AU - Togashi, Ryo
AU - Ishikawa, Soya
AU - Kochi, Takuya
AU - Kakiuchi, Fumitoshi
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI Grant Numbers JP17K19126 and JP15H05839 (Middle Molecular Strategy). T.K. is also grateful for support by JSPS KAKENHI Grant Numbers JP16H01040 and JP18H04271 (Precisely Designed Catalysts with Customized Scaffolding). S.O. is also grateful for support by JSPS Grant-in-Aid for JSPS Fellows Grant Number JP19J13174.
Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/4/22
Y1 - 2020/4/22
N2 - A method for catalytic conversion of C(aryl)-C(alkenyl) bonds in styrene derivatives to new C-C bonds is developed. In the presence of a rhodium catalyst, the alkenyl groups of styrenes bearing a pyrazolyl directing group were efficiently converted to other carbon substituents upon reacting with various alkenes including styrenes, aliphatic alkenes, and allyl alcohols. It is also indicated that the C-C bond cleavage proceeded via a hydrometalation/β-carbon elimination pathway.
AB - A method for catalytic conversion of C(aryl)-C(alkenyl) bonds in styrene derivatives to new C-C bonds is developed. In the presence of a rhodium catalyst, the alkenyl groups of styrenes bearing a pyrazolyl directing group were efficiently converted to other carbon substituents upon reacting with various alkenes including styrenes, aliphatic alkenes, and allyl alcohols. It is also indicated that the C-C bond cleavage proceeded via a hydrometalation/β-carbon elimination pathway.
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U2 - 10.1021/jacs.0c02232
DO - 10.1021/jacs.0c02232
M3 - Article
C2 - 32249570
AN - SCOPUS:85089390698
SN - 0002-7863
VL - 142
SP - 7345
EP - 7349
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 16
ER -