Origin of the Enhanced Reactivity in the ortho C–H Borylation of Benzaldehydes with BBr3

Ken Yamazaki; Supriya Rej; Yusuke Ano; Naoto Chatani

doi:10.1021/acs.orglett.1c03829

Origin of the Enhanced Reactivity in the ortho C–H Borylation of Benzaldehydes with BBr₃

Ken Yamazaki, Supriya Rej, Yusuke Ano, Naoto Chatani

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

5 Citations (Scopus)

Abstract

The metal-free ortho C–H borylation of benzaldehyde derivatives using a transient imine directing group was recently developed by our group, providing an efficient strategy for the synthesis of organoboron reagents. Herein, we report on an extensive investigation of the reaction mechanism using density functional theory (DFT) calculations.

Original language	English
Pages (from-to)	213-217
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.1c03829
Publication status	Published - Jan 14 2022
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c03829

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abstract = "The metal-free ortho C–H borylation of benzaldehyde derivatives using a transient imine directing group was recently developed by our group, providing an efficient strategy for the synthesis of organoboron reagents. Herein, we report on an extensive investigation of the reaction mechanism using density functional theory (DFT) calculations.",

author = "Ken Yamazaki and Supriya Rej and Yusuke Ano and Naoto Chatani",

note = "Funding Information: This work was supported by a Grant in Aid for Specially Promoted Research by MEXT (17H06091) and The Naito Foundation. S.R. expresses his special thanks for a JSPS Postdoctoral Research Fellowship (P19330). The supercomputer of ACCMS at Kyoto University was used in this study. Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

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AU - Yamazaki, Ken

AU - Rej, Supriya

AU - Ano, Yusuke

AU - Chatani, Naoto

N1 - Funding Information: This work was supported by a Grant in Aid for Specially Promoted Research by MEXT (17H06091) and The Naito Foundation. S.R. expresses his special thanks for a JSPS Postdoctoral Research Fellowship (P19330). The supercomputer of ACCMS at Kyoto University was used in this study. Publisher Copyright: © 2021 American Chemical Society

PY - 2022/1/14

Y1 - 2022/1/14

N2 - The metal-free ortho C–H borylation of benzaldehyde derivatives using a transient imine directing group was recently developed by our group, providing an efficient strategy for the synthesis of organoboron reagents. Herein, we report on an extensive investigation of the reaction mechanism using density functional theory (DFT) calculations.

AB - The metal-free ortho C–H borylation of benzaldehyde derivatives using a transient imine directing group was recently developed by our group, providing an efficient strategy for the synthesis of organoboron reagents. Herein, we report on an extensive investigation of the reaction mechanism using density functional theory (DFT) calculations.

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Origin of the Enhanced Reactivity in the ortho C–H Borylation of Benzaldehydes with BBr₃

Abstract

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