Issue 4, 2015
From the journal:

Chemical Science

Rhodium-catalyzed C–H functionalization-based approach to eight-membered lactams†

Shangze Wu,a   Rong Zeng,a   Chunling Fu,a   Yihua Yu,c   Xue Zhang*b  and  Shengming Ma*ab  

* Corresponding authors

a Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. China
E-mail: masm@sioc.ac.cn

b State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
E-mail: xzhang@sioc.ac.cn

c Shanghai Key Laboratory of Magnetic Resonance, Department of Physics, East China Normal University, Shanghai 200062, P. R. China

Abstract

A Rh(III) catalyzed formal [4 + 2 + 2] cyclization of N-pivaloyloxybenzamides 1 with 1,6-allene-enes 2 by C–H functionalization is reported. The reactions occur at room temperature and are compatible with air and moisture with a tolerance of many synthetically useful functional groups. The follow-up modifications of the products have been demonstrated. After careful mechanistic studies and DFT calculation, a reaction mechanism was proposed.

Graphical abstract: Rhodium-catalyzed C–H functionalization-based approach to eight-membered lactams

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Article information

DOI
https://doi.org/10.1039/C5SC00092K
Article type
Edge Article
Submitted
10 Jan 2015
Accepted
05 Feb 2015
First published
05 Feb 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 2275-2285

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Rhodium-catalyzed C–H functionalization-based approach to eight-membered lactams

S. Wu, R. Zeng, C. Fu, Y. Yu, X. Zhang and S. Ma, Chem. Sci., 2015, 6, 2275 DOI: 10.1039/C5SC00092K

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