Palladium-catalyzed ortho-selective C-H borylation of 2-phenylpyridine and its derivatives at room temperature

Yoichiro Kuninobu; Takashi Iwanaga; Tetsuya Omura; Kazuhiko Takai

doi:10.1002/anie.201210328

Palladium-catalyzed ortho-selective C-H borylation of 2-phenylpyridine and its derivatives at room temperature

Yoichiro Kuninobu, Takashi Iwanaga, Tetsuya Omura, Kazuhiko Takai

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

77 Citations (Scopus)

Abstract

Boron delivery: C-H borylation at the ortho-position of aromatic compounds is promoted by the treatment of 2-phenylpyridine, or its derivatives, with 9-borabicyclo[3.3.1]nonane in the presence of a palladium catalyst. This reaction proceeds at room temperature and can be conducted without the palladium catalyst at higher temperatures. In both cases, the regioselectivity is controlled by Lewis acid-base interaction between the boron and nitrogen atoms.

Original language	English
Pages (from-to)	4431-4434
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	16
DOIs	https://doi.org/10.1002/anie.201210328
Publication status	Published - Apr 15 2013

Keywords

Lewis acid
Lewis base
borylation
palladium
regioselectivity

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201210328

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abstract = "Boron delivery: C-H borylation at the ortho-position of aromatic compounds is promoted by the treatment of 2-phenylpyridine, or its derivatives, with 9-borabicyclo[3.3.1]nonane in the presence of a palladium catalyst. This reaction proceeds at room temperature and can be conducted without the palladium catalyst at higher temperatures. In both cases, the regioselectivity is controlled by Lewis acid-base interaction between the boron and nitrogen atoms.",

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AU - Omura, Tetsuya

AU - Takai, Kazuhiko

PY - 2013/4/15

Y1 - 2013/4/15

N2 - Boron delivery: C-H borylation at the ortho-position of aromatic compounds is promoted by the treatment of 2-phenylpyridine, or its derivatives, with 9-borabicyclo[3.3.1]nonane in the presence of a palladium catalyst. This reaction proceeds at room temperature and can be conducted without the palladium catalyst at higher temperatures. In both cases, the regioselectivity is controlled by Lewis acid-base interaction between the boron and nitrogen atoms.

AB - Boron delivery: C-H borylation at the ortho-position of aromatic compounds is promoted by the treatment of 2-phenylpyridine, or its derivatives, with 9-borabicyclo[3.3.1]nonane in the presence of a palladium catalyst. This reaction proceeds at room temperature and can be conducted without the palladium catalyst at higher temperatures. In both cases, the regioselectivity is controlled by Lewis acid-base interaction between the boron and nitrogen atoms.

KW - Lewis acid

KW - Lewis base

KW - borylation

KW - palladium

KW - regioselectivity

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Palladium-catalyzed ortho-selective C-H borylation of 2-phenylpyridine and its derivatives at room temperature

Abstract

Keywords

ASJC Scopus subject areas

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