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Application of Fundamental Organometallic Chemistry to the Development of a Gold‐Catalyzed Synthesis of Sulfinate Derivatives
Author(s) -
Johnson Miles W.,
Bagley Scott W.,
Mankad Neal P.,
Bergman Robert G.,
Mascitti Vincent,
Toste F. Dean
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400037
Subject(s) - chemistry , pharmacophore , aryl , heteroatom , combinatorial chemistry , catalysis , reactivity (psychology) , organic chemistry , stereochemistry , ring (chemistry) , alkyl , medicine , alternative medicine , pathology
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.