Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

Jialin Zeng; Morio Naito; Takeru Torigoe; Masahiro Yamanaka; Yoichiro Kuninobu

doi:10.1021/acs.orglett.0c00946

Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

Jialin Zeng, Morio Naito, Takeru Torigoe, Masahiro Yamanaka, Yoichiro Kuninobu

Department of Fundamental Organic Chemistry

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

13 Citations (Scopus)

Abstract

A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH₃ group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

Original language	English
Pages (from-to)	3485-3489
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.0c00946
Publication status	Published - May 1 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c00946

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title = "Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand",

abstract = "A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.",

author = "Jialin Zeng and Morio Naito and Takeru Torigoe and Masahiro Yamanaka and Yoichiro Kuninobu",

note = "Funding Information: This work was partially supported by JSPS KAKENHI grant numbers JP 17H03016, 18H04656, and 18H04660 and the Yamada Science Foundation. Publisher Copyright: {\textcopyright} 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

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AU - Naito, Morio

AU - Torigoe, Takeru

AU - Yamanaka, Masahiro

AU - Kuninobu, Yoichiro

N1 - Funding Information: This work was partially supported by JSPS KAKENHI grant numbers JP 17H03016, 18H04656, and 18H04660 and the Yamada Science Foundation. Publisher Copyright: © 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/5/1

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N2 - A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

AB - A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

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Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

Abstract

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