Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids

Naoki Oku; Masahiro Murakami; Tomoya Miura

doi:10.1021/acs.orglett.2c00121

Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids

Naoki Oku, Masahiro Murakami, Tomoya Miura

School of Engineering

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

6 Citations (Scopus)

Abstract

A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.

Original language	English
Pages (from-to)	1616-1619
Number of pages	4
Journal	Organic Letters
Volume	24
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.2c00121
Publication status	Published - Mar 4 2022

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c00121

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title = "Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids",

abstract = "A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.",

author = "Naoki Oku and Masahiro Murakami and Tomoya Miura",

note = "Funding Information: We thank Mr. N. Kamiya (Kyoto University) for his kind help with UV–vis analysis. This work was supported in part by JSPS KAKENHI [Grants-in-Aid for Scientific Research (B) (20H02739) (T.M.)]. N.O. acknowledges Kyoto University Science and Technology Innovation Creation Fellowship: Material Science. Publisher Copyright: {\textcopyright} 2022 American Chemical Society",

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doi = "10.1021/acs.orglett.2c00121",

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AU - Oku, Naoki

AU - Murakami, Masahiro

AU - Miura, Tomoya

N1 - Funding Information: We thank Mr. N. Kamiya (Kyoto University) for his kind help with UV–vis analysis. This work was supported in part by JSPS KAKENHI [Grants-in-Aid for Scientific Research (B) (20H02739) (T.M.)]. N.O. acknowledges Kyoto University Science and Technology Innovation Creation Fellowship: Material Science. Publisher Copyright: © 2022 American Chemical Society

PY - 2022/3/4

Y1 - 2022/3/4

N2 - A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.

AB - A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.

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JO - Organic Letters

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Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids

Abstract

ASJC Scopus subject areas

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