Iron/Copper co-catalyzed synthesis of vinyl sulfones from sulfonyl hydrazides and alkyne derivatives

Guangwei Rong; Jincheng Mao; Hong Yan; Yang Zheng; Guoqi Zhang

doi:10.1021/acs.joc.5b00558

Iron/Copper co-catalyzed synthesis of vinyl sulfones from sulfonyl hydrazides and alkyne derivatives

J Org Chem. 2015 May 1;80(9):4697-703. doi: 10.1021/acs.joc.5b00558. Epub 2015 Apr 22.

Authors

Guangwei Rong¹, Jincheng Mao^{1

2}, Hong Yan¹, Yang Zheng¹, Guoqi Zhang³

Affiliations

¹ †Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, Suzhou 215123, P. R. China.
² ‡State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu, 610500, P. R. China.
³ §Department of Sciences, John Jay College and The Graduate Center, The City University of New York, New York, New York 10019, United States.

PMID: 25876519
DOI: 10.1021/acs.joc.5b00558

Abstract

A new approach to the selective synthesis of (E)-vinyl sulfones has been developed via a Fe/Cu co-catalyzed sulfonylation of arylpropiolic acid or phenylacetylene with sulfonyl hydrazides. A variety of vinyl sulfones have been obtained in moderate to good yields, comparable to the best results reported so far. The inexpensive Fe/Cu co-catalyzed method features a simple experimental procedure and good tolerance of substrate.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Catalysis
Copper / chemistry*
Hydrazines / chemistry*
Iron / chemistry*
Molecular Structure
Sulfones / chemical synthesis
Sulfones / chemistry*

Substances

Alkynes
Hydrazines
Sulfones
divinyl sulfone
Copper
Iron