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Issue 3, 2016
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Metal-free oxidative hydrophosphinylation of 1,7-enynes

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Abstract

A new metal-free oxidative hydrophosphinylation of 1,7-enynes for forming polyfunctionalized 3,4-dihydroquinolin-2(1H)-ones has been realized using readily accessible diarylphosphine oxide and TBPB as an oxidant. The reaction pathway involves an in situ-generated P-centered radical-triggered α,β-conjugate addition/6-exo-dig cyclization/H-abstraction sequence, providing a direct and promising protocol for the formation of C–P, C–C and C–H bonds and rapid construction of complex heterocyclic compounds.

Graphical abstract: Metal-free oxidative hydrophosphinylation of 1,7-enynes

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Supplementary files

Article information


Submitted
17 Dec 2015
Accepted
22 Jan 2016
First published
25 Jan 2016

Org. Chem. Front., 2016,3, 385-393
Article type
Research Article

Metal-free oxidative hydrophosphinylation of 1,7-enynes

Y. Zhu, D. Wang, B. Jiang, W. Hao, P. Wei, A. Wang, J. Qiu and S. Tu, Org. Chem. Front., 2016, 3, 385 DOI: 10.1039/C5QO00430F

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