Issue 3, 2016

Metal-free tandem oxidative C(sp3)–H bond functionalization of alkanes and dearomatization of N-phenyl-cinnamamides: access to alkylated 1-azaspiro[4.5]decanes

Abstract

The TBPB promoted tandem oxidative C(sp3)–H bond functionalization of simple alkanes/alkylation-initiated dearomatization of N-phenyl-cinnamamides is reported, providing a direct method for the synthesis of alkylated 1-azaspiro[4.5]decanes with excellent regioselectivity and diastereoselectivity. The formation of two C(sp3)–C(sp3) bonds and construction of a spirodienone motif are involved in one step.

Graphical abstract: Metal-free tandem oxidative C(sp3)–H bond functionalization of alkanes and dearomatization of N-phenyl-cinnamamides: access to alkylated 1-azaspiro[4.5]decanes

Supplementary files

Article information

Article type
Communication
Submitted
26 Aug 2015
Accepted
21 Oct 2015
First published
22 Oct 2015

Chem. Commun., 2016,52, 477-480

Author version available

Metal-free tandem oxidative C(sp3)–H bond functionalization of alkanes and dearomatization of N-phenyl-cinnamamides: access to alkylated 1-azaspiro[4.5]decanes

H. Zhang, Z. Gu, P. Xu, H. Hu, Y. Cheng and C. Zhu, Chem. Commun., 2016, 52, 477 DOI: 10.1039/C5CC07175E

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