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; P. Quayle

doi:10.1039/C5OB01239B

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, P. Quayle

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

Abstract

Treatment of ortho-(trimethysilyl)aryl phenylsulfonates with a sol. fluoride source initiates a Truce-Smiles rearrangement leading to the formation of functionalized bi-aryls [e.g., I → II (74%)]. This new carbon-carbon bond-forming reaction proceeds without recourse to transition metal catalysis, under mild reaction conditions and with good functional group compatibility. Safety: precautions should be taken in handling poly-nitro aroms. to avoid detonation.

Original language	English
Pages (from-to)	8048-8052
Number of pages	4
Journal	Organic & biomolecular chemistry
Volume	13
DOIs	https://doi.org/10.1039/C5OB01239B
Publication status	Published - 2015

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title = "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 sol. fluoride source initiates a Truce-Smiles rearrangement leading to the formation of functionalized bi-aryls [e.g., I → II (74%)]. This new carbon-carbon bond-forming reaction proceeds without recourse to transition metal catalysis, under mild reaction conditions and with good functional group compatibility. Safety: precautions should be taken in handling poly-nitro aroms. to avoid detonation.",

author = "Rasheed, {O. K.} and Hardcastle, {I. R.} and J. Raftery and P. Quayle",

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AU - Rasheed, O. K.

AU - Hardcastle, I. R.

AU - Raftery, J.

AU - Quayle, P.

PY - 2015

Y1 - 2015

N2 - Treatment of ortho-(trimethysilyl)aryl phenylsulfonates with a sol. fluoride source initiates a Truce-Smiles rearrangement leading to the formation of functionalized bi-aryls [e.g., I → II (74%)]. This new carbon-carbon bond-forming reaction proceeds without recourse to transition metal catalysis, under mild reaction conditions and with good functional group compatibility. Safety: precautions should be taken in handling poly-nitro aroms. to avoid detonation.

AB - Treatment of ortho-(trimethysilyl)aryl phenylsulfonates with a sol. fluoride source initiates a Truce-Smiles rearrangement leading to the formation of functionalized bi-aryls [e.g., I → II (74%)]. This new carbon-carbon bond-forming reaction proceeds without recourse to transition metal catalysis, under mild reaction conditions and with good functional group compatibility. Safety: precautions should be taken in handling poly-nitro aroms. to avoid detonation.

U2 - 10.1039/C5OB01239B

DO - 10.1039/C5OB01239B

M3 - Article

SN - 1477-0520

VL - 13

SP - 8048

EP - 8052

JO - Organic & biomolecular chemistry

JF - Organic & biomolecular chemistry

ER -

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

Abstract

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