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Issue 3, 2016
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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

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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

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Article information


Submitted
26 Aug 2015
Accepted
21 Oct 2015
First published
22 Oct 2015

Chem. Commun., 2016,52, 477-480
Article type
Communication
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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