Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds

Ayan Dasgupta; Katarína Stefkova; Rasool Babaahmadi; Lukas Gierlichs; Alireza Ariafard; Rebecca L. Melen

doi:10.1002/anie.202007176

Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds

Ayan Dasgupta, Katarína Stefkova, Rasool Babaahmadi, Lukas Gierlichs, Alireza Ariafard^*, Rebecca L. Melen^*

^*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.

Original language	English
Pages (from-to)	15492-15496
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	36
DOIs	https://doi.org/10.1002/anie.202007176
Publication status	Published - 2020
Externally published	Yes

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title = "Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds",

abstract = "Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol \%) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 \%). DFT studies were used to elucidate the mechanism for this alkenylation reaction.",

keywords = "alkenylation, diazoesters, metal-free catalysis, tris(pentafluorophenyl)borane",

author = "Ayan Dasgupta and Katar{\'i}na Stefkova and Rasool Babaahmadi and Lukas Gierlichs and Alireza Ariafard and Melen, \{Rebecca L.\}",

note = "Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH Verlag GmbH \& Co. KGaA",

year = "2020",

doi = "10.1002/anie.202007176",

language = "English",

volume = "59",

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AU - Dasgupta, Ayan

AU - Stefkova, Katarína

AU - Babaahmadi, Rasool

AU - Gierlichs, Lukas

AU - Ariafard, Alireza

AU - Melen, Rebecca L.

PY - 2020

Y1 - 2020

N2 - Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.

AB - Herein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.

KW - alkenylation

KW - diazoesters

KW - metal-free catalysis

KW - tris(pentafluorophenyl)borane

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VL - 59

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 36

ER -

Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds

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