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Application of fundamental organometallic chemistry to the development of a gold-catalyzed synthesis of sulfinate derivatives.

ABSTRACT: The development of a gold(I)-catalyzed sulfination of aryl boronic acids is described. This transformation proceeds through an unprecedented mechanism which exploits the reactivity of gold(I)-heteroatom bonds to form sulfinate anions. Further in situ elaboration of the sulfinate intermediates leads to the corresponding sulfones and sulfonamides, two pharmacophores routinely encountered in drug discovery.

SUBMITTER: Johnson MW

PROVIDER: S-EPMC5089845 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Application of fundamental organometallic chemistry to the development of a gold-catalyzed synthesis of sulfinate derivatives.

Johnson Miles W MW Bagley Scott W SW Mankad Neal P NP Bergman Robert G RG Mascitti Vincent V Toste F Dean FD

Angewandte Chemie (International ed. in English) 20140320 17

The development of a gold(I)-catalyzed sulfination of aryl boronic acids is described. This transformation proceeds through an unprecedented mechanism which exploits the reactivity of gold(I)-heteroatom bonds to form sulfinate anions. Further in situ elaboration of the sulfinate intermediates leads to the corresponding sulfones and sulfonamides, two pharmacophores routinely encountered in drug discovery. ...[more]

PMID: 24652820

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