Copper-Catalyzed Alkynylation of Benzylic C–H Bonds with Alkynylboronic Esters

Mikkel Burggraaf Buendia; Jan-Georges J. Balin; Mette E. Andersen; Zhong Lian; Søren Kramer

doi:10.1055/s-0040-1720474

Copper-Catalyzed Alkynylation of Benzylic C–H Bonds with Alkynylboronic Esters

Mikkel Burggraaf Buendia, Jan-Georges J. Balin, Mette E. Andersen, Zhong Lian, Søren Kramer^*

^*Corresponding author for this work

Department of Chemistry

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Abstract

We report a simple method for copper-catalyzed benzylic C–H alkynylation that uses alkynylboronic esters as nucleophilic coupling partners. The catalytic system is readily available and the reaction takes place under mild conditions. Different substrates for the C–H functionalization, as well as various alkynylboronic ester nucleophiles, were evaluated. Finally, three examples of enantioselective C–H alkynylations are presented.

Original language	English
Journal	Synlett
Volume	33
Issue number	2
Pages (from-to)	150-154
Number of pages	5
ISSN	0936-5214
DOIs	https://doi.org/10.1055/s-0040-1720474
Publication status	Published - 2022

Bibliographical note

S.K. is deeply appreciative of financial support from the Lundbeck Foundation (grant no. R250-2017-1292), the Independent Research Fund Denmark (grant no. 0171-00018B), and the Villum Foundation (grant no. 35812). Z.L. thanks the National Natural Science Foundation of China (21901168), the ‘1000-Youth Talents Plan’, Sichuan Science and Technology Program (2021YJ0395), and Sichuan University for generous financial support.

Keywords

C–H functionalization
copper catalysis
alkynylation
homogeneous catalysis
boronic esters

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title = "Copper-Catalyzed Alkynylation of Benzylic C–H Bonds with Alkynylboronic Esters",

abstract = "We report a simple method for copper-catalyzed benzylic C–H alkynylation that uses alkynylboronic esters as nucleophilic coupling partners. The catalytic system is readily available and the reaction takes place under mild conditions. Different substrates for the C–H functionalization, as well as various alkynylboronic ester nucleophiles, were evaluated. Finally, three examples of enantioselective C–H alkynylations are presented.",

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note = "S.K. is deeply appreciative of financial support from the Lundbeck Foundation (grant no. R250-2017-1292), the Independent Research Fund Denmark (grant no. 0171-00018B), and the Villum Foundation (grant no. 35812). Z.L. thanks the National Natural Science Foundation of China (21901168), the {\textquoteleft}1000-Youth Talents Plan{\textquoteright}, Sichuan Science and Technology Program (2021YJ0395), and Sichuan University for generous financial support.",

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doi = "10.1055/s-0040-1720474",

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T1 - Copper-Catalyzed Alkynylation of Benzylic C–H Bonds with Alkynylboronic Esters

AU - Buendia, Mikkel Burggraaf

AU - Balin, Jan-Georges J.

AU - Andersen, Mette E.

AU - Lian, Zhong

AU - Kramer, Søren

N1 - S.K. is deeply appreciative of financial support from the Lundbeck Foundation (grant no. R250-2017-1292), the Independent Research Fund Denmark (grant no. 0171-00018B), and the Villum Foundation (grant no. 35812). Z.L. thanks the National Natural Science Foundation of China (21901168), the ‘1000-Youth Talents Plan’, Sichuan Science and Technology Program (2021YJ0395), and Sichuan University for generous financial support.

PY - 2022

Y1 - 2022

N2 - We report a simple method for copper-catalyzed benzylic C–H alkynylation that uses alkynylboronic esters as nucleophilic coupling partners. The catalytic system is readily available and the reaction takes place under mild conditions. Different substrates for the C–H functionalization, as well as various alkynylboronic ester nucleophiles, were evaluated. Finally, three examples of enantioselective C–H alkynylations are presented.

AB - We report a simple method for copper-catalyzed benzylic C–H alkynylation that uses alkynylboronic esters as nucleophilic coupling partners. The catalytic system is readily available and the reaction takes place under mild conditions. Different substrates for the C–H functionalization, as well as various alkynylboronic ester nucleophiles, were evaluated. Finally, three examples of enantioselective C–H alkynylations are presented.

KW - C–H functionalization

KW - copper catalysis

KW - alkynylation

KW - homogeneous catalysis

KW - boronic esters

U2 - 10.1055/s-0040-1720474

DO - 10.1055/s-0040-1720474

M3 - Journal article

VL - 33

SP - 150

EP - 154

JO - SYNLETT: Accounts and Rapid Communications in Chemical Synthesis

JF - SYNLETT: Accounts and Rapid Communications in Chemical Synthesis

SN - 0936-5214

IS - 2

ER -

Copper-Catalyzed Alkynylation of Benzylic C–H Bonds with Alkynylboronic Esters

Abstract

Bibliographical note

Keywords

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