Issue 29, 2015

Aryne generation vs. Truce-Smiles and fries rearrangements during the Kobayashi fragmentation reaction: a new bi-aryl synthesis

Abstract

Treatment of (ortho-trimethysilyl)aryl phenylsulfonates with a soluble fluoride source initiates a Truce-Smiles rearrangement leading to the formation of functionalized bi-aryls. This new carbon–carbon bond-forming reaction proceeds without recourse to transition metal catalysis, under mild reaction conditions and with good functional group compatibility.

Graphical abstract: Aryne generation vs. Truce-Smiles and fries rearrangements during the Kobayashi fragmentation reaction: a new bi-aryl synthesis

Supplementary files

Article information

Article type
Paper
Submitted
17 Jun 2015
Accepted
18 Jun 2015
First published
18 Jun 2015

Org. Biomol. Chem., 2015,13, 8048-8052

Author version available

Aryne generation vs. Truce-Smiles and fries rearrangements during the Kobayashi fragmentation reaction: a new bi-aryl synthesis

O. K. Rasheed, I. R. Hardcastle, J. Raftery and P. Quayle, Org. Biomol. Chem., 2015, 13, 8048 DOI: 10.1039/C5OB01239B

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