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J Org Chem. 2016 Jan 4;81(1):66-76. doi: 10.1021/acs.joc.5b02161. Epub 2015 Dec 17.

Iodine-Promoted Radical Cyclization in Water: A Selective Reaction of 1,6-Enynes with Sulfonyl Hydrazides.

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1
State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, PR China.

Abstract

An iodine-promoted one-pot radical cyclization reaction of 1,6-enynes with sulfonyl hydrazides to provide five-membered and hexatomic ring sulfonylated products under the same conditions is established. This reaction proceeded smoothly in water and gave the corresponding products by using I2/TBHP instead of expensive and toxic catalysts with C-S and C-I bond formed in one step. This method also allowed easy access to significant functional sulfones for potential applications in medicinal and organic chemistry.

PMID:
26642246
DOI:
10.1021/acs.joc.5b02161

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