Metal Free Bi-(hetero)aryl Synthesis via Benzyne Truce-Smiles Rearrangement

M. F. Greaney; C. M. Holden; S. A. M. Sohel

doi:10.1002/anie.201510236

Metal Free Bi-(hetero)aryl Synthesis via Benzyne Truce-Smiles Rearrangement

M. F. Greaney, C. M. Holden, S. A. M. Sohel

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

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.

Original language	English
Pages (from-to)	2450-2453
Journal	Angewandte Chemie (International Edition)
Volume	55
DOIs	https://doi.org/10.1002/anie.201510236
Publication status	Published - 13 Jan 2016

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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.",

author = "Greaney, {M. F.} and Holden, {C. M.} and Sohel, {S. A. M.}",

note = "Supporting information for this article is available on the WWW under http://www.angewandte.org or from the author.",

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AU - Holden, C. M.

AU - Sohel, S. A. M.

N1 - Supporting information for this article is available on the WWW under http://www.angewandte.org or from the author.

PY - 2016/1/13

Y1 - 2016/1/13

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AB - 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.

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DO - 10.1002/anie.201510236

M3 - Article

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JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

ER -

Metal Free Bi-(hetero)aryl Synthesis via Benzyne Truce-Smiles Rearrangement

Abstract

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