Palladium(II)-Catalyzed Intramolecular Tandem Aminoalkylation via Divergent C(sp3)–H Functionalization

We have developed a Pd(II)-catalyzed oxidative tandem aminoalkylation via divergent C(sp3)–H functionalization, affording three- and five-membered-ring fused indolines in good yields under two optimized conditions, respectively. The mechanism studies have indicated that the benzylic C–H cleavage inv...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-01, Vol.137 (3), p.1130-1135
Main Authors: Du, Wei, Gu, Qiangshuai, Li, Zhongliang, Yang, Dan
Format: Article
Language:English
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Summary:We have developed a Pd(II)-catalyzed oxidative tandem aminoalkylation via divergent C(sp3)–H functionalization, affording three- and five-membered-ring fused indolines in good yields under two optimized conditions, respectively. The mechanism studies have indicated that the benzylic C–H cleavage involved in the former transformation is the rate-determining step, while the cleavage of amide α-C–H in the latter is not. This is the first example of a Pd-catalyzed tandem reaction involving C(sp3)–H activation without the employment of prefunctionalized reagents (e.g., halogenated and boron reagents) and directing groups, representing a green and economic protocol for the construction of N-containing heterocycles.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja5102739