TY - JOUR
T1 - Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp2)-H and C(sp3)-O Bonds
AU - Dong, Xunqing
AU - Li, Qun
AU - Li, Guigen
AU - Lu, Hongjian
N1 - Funding Information:
We would like to acknowledge the financial support from the National Natural Science Foundation of China (21332005, 21472085 and 21672100) and the Fundamental Research Funds for the Central Universities (020514380131).
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/11/2
Y1 - 2018/11/2
N2 - A novel cobalt-catalyzed C-H alkylation of arenes and olefins is achieved with (pyridin-2-yl)isopropyl amine as an N,N-bidentate directing group. Different linear, branched, and cyclic alkyl ethers were used as practical secondary alkylating reagents through cleavage of C(sp3)-O bond, providing an efficient approach to the synthesis of verstile o-alkylated arylamides and tetrasubstituted acrylamides. Mechanistic studies indicate that cleavage of the inert C(sp3)-O bond involves a cobalt-promoted radical process and that cleavage of the inert C(sp2)-H bond by a cobalt catalyst is a rate-limiting step.
AB - A novel cobalt-catalyzed C-H alkylation of arenes and olefins is achieved with (pyridin-2-yl)isopropyl amine as an N,N-bidentate directing group. Different linear, branched, and cyclic alkyl ethers were used as practical secondary alkylating reagents through cleavage of C(sp3)-O bond, providing an efficient approach to the synthesis of verstile o-alkylated arylamides and tetrasubstituted acrylamides. Mechanistic studies indicate that cleavage of the inert C(sp3)-O bond involves a cobalt-promoted radical process and that cleavage of the inert C(sp2)-H bond by a cobalt catalyst is a rate-limiting step.
UR - http://www.scopus.com/inward/record.url?scp=85055902474&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b02197
DO - 10.1021/acs.joc.8b02197
M3 - Article
C2 - 30351937
AN - SCOPUS:85055902474
VL - 83
SP - 13402
EP - 13413
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 21
ER -