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Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement.

ABSTRACT: A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines.

SUBMITTER: Holden CM

PROVIDER: S-EPMC4819888 | biostudies-other | 2016 Feb

REPOSITORIES: biostudies-other

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Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement.

Holden Catherine M CM Sohel Shariar M A SM Greaney Michael F MF

Angewandte Chemie (International ed. in English) 20160113 7

A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines. ...[more]

PMID: 26762551

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