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Rhodium(III)‐Catalyzed [3+2] Annulation of 5‐Aryl‐2,3‐dihydro‐1 H ‐pyrroles with Internal Alkynes through C(sp 2 )H/Alkene Functionalization
Author(s) -
Zhou MingBo,
Pi Rui,
Hu Ming,
Yang Yuan,
Song RenJie,
Xia Yuanzhi,
Li JinHeng
Publication year - 2014
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.201407175
Subject(s) - annulation , alkene , rhodium , protonolysis , chemistry , aryl , indene , pyrrolidine , catalysis , alkyne , medicinal chemistry , stereochemistry , organic chemistry , alkyl
This study describes a new rhodium(III)‐catalyzed [3+2] annulation of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles with internal alkynes using a Cu(OAc) 2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp 2 )H bond and addition/protonolysis of an alkene CC bond. This method is applicable to a wide range of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles and internal alkynes, and results in the assembly of the spiro[indene‐1,2′‐pyrrolidine] architectures in good yields with excellent regioselectivities.