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Nitrone Directing Groups in Rhodium(III)‐Catalyzed C−H Activation of Arenes: 1,3‐Dipoles versus Traceless Directing Groups
Author(s) -
Xie Fang,
Yu Songjie,
Qi Zisong,
Li Xingwei
Publication year - 2016
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.201609658
Subject(s) - nitrone , rhodium , acylation , chemistry , substituent , catalysis , medicinal chemistry , coupling reaction , stereochemistry , combinatorial chemistry , organic chemistry , cycloaddition
Functionalizable directing groups (DGs) are highly desirable in C−H activation chemistry. The nitrone DGs are explored in rhodium(III)‐catalyzed C−H activation of arenes and couplings with cyclopropenones. N‐tert ‐butyl nitrones bearing a small ortho substituent coupled to afford 1‐naphthols, where the nitrone acts as a traceless DG. In contrast, coupling of N‐tert ‐butyl nitrones bearing a bulky ortho group follows a C−H acylation/[3+2] dipolar addition pathway to give bicyclics. The coupling of N‐arylnitrones follows the same acylation/[3+2] addition process but delivers different bicyclics.