Issue 16, 2017

Oxidative bicyclization of N-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-ones via site-selective decarboxylative C(sp3)–H functionalization

Abstract

A new Ag-catalyzed oxidative bicyclization of N-tethered 1,7-enynes with alkylcarboxylic acids for forming 41 examples of polycyclic 3,4-dihydroquinolin-2(1H)-ones has been established using readily accessible K2S2O8 as an oxidant. The reaction pathway involves a silver-catalyzed decarboxylation/in situ-generated C-center radical-triggered α,β-conjugated addition/6-exo-dig cyclization/H-abstraction/5-endo-trig cyclization/SET sequence, allowing direct site-selective decarboxylative C(sp3)–H functionalization toward the formation of multiple C–C bonds and rapid construction of complex spiroheterocycles.

Graphical abstract: Oxidative bicyclization of N-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-ones via site-selective decarboxylative C(sp3)–H functionalization

Supplementary files

Article information

Article type
Paper
Submitted
22 dic. 2016
Accepted
28 ene. 2017
First published
02 feb. 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 9693-9703

Oxidative bicyclization of N-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-ones via site-selective decarboxylative C(sp3)–H functionalization

J. Li, W. Hao, P. Zhou, Y. Zhu, S. Wang, S. Tu and B. Jiang, RSC Adv., 2017, 7, 9693 DOI: 10.1039/C6RA28589A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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