Issue 3, 2016
From the journal:

Organic Chemistry Frontiers

Metal-free oxidative hydrophosphinylation of 1,7-enynes†

Yi-Long Zhu,‡ab   De-Cai Wang,‡a   Bo Jiang,*b   Wen-Juan Hao,b   Ping Wei,*a   Ai-Fang Wang,b   Jiang-Kai Qiuab  and  Shu-Jiang Tu*b  

* Corresponding authors

a Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, Jiangsu, P. R. China
E-mail: weiping@njtech.edu.cn

b School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China
E-mail: jiangchem@jsnu.edu.cn, laotu@jsnu.edu.cn
Fax: +86 51683500065
Tel: +86 51683500065

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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Article information

DOI
https://doi.org/10.1039/C5QO00430F
Article type
Research Article
Submitted
17 Dec 2015
Accepted
22 Jan 2016
First published
25 Jan 2016

Org. Chem. Front., 2016,3, 385-393

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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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