Trichloroacetonitrile as an efficient activating agent for the: Ipso -hydroxylation of arylboronic acids to phenolic compounds

Yuanding Fang; Rong Zhao; Yuan Yao; Yang Liu; Denghu Chang; Ming Yao; Lei Shi

doi:10.1039/c9ob01568j

Trichloroacetonitrile as an efficient activating agent for the: Ipso -hydroxylation of arylboronic acids to phenolic compounds

Yuanding Fang
, Rong Zhao
, Yuan Yao
, Yang Liu
, Denghu Chang
, Ming Yao
, Lei Shi^*

^*Corresponding author for this work

Harbin Institute of Technology
School of Chemistry and Chemical Engineering, Harbin Institute of Technology
Jingchu University of Technology
Peking University

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

17 Scopus citations

Abstract

A metal-free and base-free Cl₃CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.

Original language	English
Pages (from-to)	7558-7563
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	32
DOIs	https://doi.org/10.1039/c9ob01568j
State	Published - 2019
Externally published	Yes

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title = "Trichloroacetonitrile as an efficient activating agent for the: Ipso -hydroxylation of arylboronic acids to phenolic compounds",

abstract = "A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.",

author = "Yuanding Fang and Rong Zhao and Yuan Yao and Yang Liu and Denghu Chang and Ming Yao and Lei Shi",

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T2 - Ipso -hydroxylation of arylboronic acids to phenolic compounds

AU - Fang, Yuanding

AU - Zhao, Rong

AU - Yao, Yuan

AU - Liu, Yang

AU - Chang, Denghu

AU - Yao, Ming

AU - Shi, Lei

PY - 2019

Y1 - 2019

N2 - A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.

AB - A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.

UR - https://www.scopus.com/pages/publications/85070691584

U2 - 10.1039/c9ob01568j

DO - 10.1039/c9ob01568j

M3 - 文章

C2 - 31373339

AN - SCOPUS:85070691584

SN - 1477-0520

VL - 17

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 32

ER -

Trichloroacetonitrile as an efficient activating agent for the: Ipso -hydroxylation of arylboronic acids to phenolic compounds

Abstract

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