Preparation of Alkyl Alkynyl Sulfones and Cyclic Vinyl Sulfones from Alkynyl(aryl)iodonium Salts

Arantxa Rodríguez; Wesley J. Moran

doi:10.1021/acs.joc.6b00124

Preparation of Alkyl Alkynyl Sulfones and Cyclic Vinyl Sulfones from Alkynyl(aryl)iodonium Salts

Arantxa Rodríguez, Wesley J. Moran

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

The reaction of alkyl sulfinates with alkynyl(aryl)iodonium salts provides a facile access into otherwise difficult to obtain alkyl alkynyl sulfones and cyclic vinyl sulfones via 1,2-rearrangement or 1,5-CH insertion, respectively. In benzyl sulfinates, 1,5-CH insertion is not possible, so addition to the aromatic ring occurs, followed by ring expansion to generate novel bicyclic sulfones.

Original language	English
Pages (from-to)	2543-2548
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	81
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.6b00124
Publication status	Published - 29 Feb 2016

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title = "Preparation of Alkyl Alkynyl Sulfones and Cyclic Vinyl Sulfones from Alkynyl(aryl)iodonium Salts",

abstract = "The reaction of alkyl sulfinates with alkynyl(aryl)iodonium salts provides a facile access into otherwise difficult to obtain alkyl alkynyl sulfones and cyclic vinyl sulfones via 1,2-rearrangement or 1,5-CH insertion, respectively. In benzyl sulfinates, 1,5-CH insertion is not possible, so addition to the aromatic ring occurs, followed by ring expansion to generate novel bicyclic sulfones.",

author = "Arantxa Rodr{\'i}guez and Moran, \{Wesley J.\}",

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Y1 - 2016/2/29

N2 - The reaction of alkyl sulfinates with alkynyl(aryl)iodonium salts provides a facile access into otherwise difficult to obtain alkyl alkynyl sulfones and cyclic vinyl sulfones via 1,2-rearrangement or 1,5-CH insertion, respectively. In benzyl sulfinates, 1,5-CH insertion is not possible, so addition to the aromatic ring occurs, followed by ring expansion to generate novel bicyclic sulfones.

AB - The reaction of alkyl sulfinates with alkynyl(aryl)iodonium salts provides a facile access into otherwise difficult to obtain alkyl alkynyl sulfones and cyclic vinyl sulfones via 1,2-rearrangement or 1,5-CH insertion, respectively. In benzyl sulfinates, 1,5-CH insertion is not possible, so addition to the aromatic ring occurs, followed by ring expansion to generate novel bicyclic sulfones.

UR - https://www.scopus.com/pages/publications/84961839311

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DO - 10.1021/acs.joc.6b00124

M3 - Article

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Preparation of Alkyl Alkynyl Sulfones and Cyclic Vinyl Sulfones from Alkynyl(aryl)iodonium Salts

Abstract

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