Ligand-Accelerated Direct C−H Arylation of BINOL: A Rapid One-Step Synthesis of Racemic 3,3′-Diaryl BINOLs

Jin Fei Yang; Rong Hua Wang; Yin Xia Wang; Wei Wei Yao; Qi Sheng Liu; Mengchun Ye

doi:10.1002/anie.201607893

Ligand-Accelerated Direct C−H Arylation of BINOL: A Rapid One-Step Synthesis of Racemic 3,3′-Diaryl BINOLs

Jin Fei Yang
, Rong Hua Wang
, Yin Xia Wang
, Wei Wei Yao
, Qi Sheng Liu
, Mengchun Ye

Nankai University
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)

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

69 Scopus citations

Abstract

An ortho-selective rhodium-catalyzed direct C−H arylation of 1,1′-bi-2-naphthol (BINOL), to deliver the widely used but not easily available 3,3′-diaryl BINOL, has been developed. This highly efficient one-step synthetic approach is the shortest route to date and is greatly facilitated by the newly developed ligand system comprising tBu₂PCl, Ph₂-cod, and Cy₃P⋅HBF₄. In addition, the same procedure can facilitate the challenging syntheses of 3-bulkyaryl BINOLs in good to excellent yields.

Original language	English
Pages (from-to)	14116-14120
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	45
DOIs	https://doi.org/10.1002/anie.201607893
State	Published - 2 Nov 2016
Externally published	Yes

Keywords

arylation
biaryls
cross-coupling
ligand design
rhodium

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10.1002/anie.201607893

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title = "Ligand-Accelerated Direct C−H Arylation of BINOL: A Rapid One-Step Synthesis of Racemic 3,3′-Diaryl BINOLs",

abstract = "An ortho-selective rhodium-catalyzed direct C−H arylation of 1,1′-bi-2-naphthol (BINOL), to deliver the widely used but not easily available 3,3′-diaryl BINOL, has been developed. This highly efficient one-step synthetic approach is the shortest route to date and is greatly facilitated by the newly developed ligand system comprising tBu2PCl, Ph2-cod, and Cy3P⋅HBF4. In addition, the same procedure can facilitate the challenging syntheses of 3-bulkyaryl BINOLs in good to excellent yields.",

keywords = "arylation, biaryls, cross-coupling, ligand design, rhodium",

author = "Yang, \{Jin Fei\} and Wang, \{Rong Hua\} and Wang, \{Yin Xia\} and Yao, \{Wei Wei\} and Liu, \{Qi Sheng\} and Mengchun Ye",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

month = nov,

day = "2",

doi = "10.1002/anie.201607893",

language = "英语",

volume = "55",

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journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Ligand-Accelerated Direct C−H Arylation of BINOL

T2 - A Rapid One-Step Synthesis of Racemic 3,3′-Diaryl BINOLs

AU - Yang, Jin Fei

AU - Wang, Rong Hua

AU - Wang, Yin Xia

AU - Yao, Wei Wei

AU - Liu, Qi Sheng

AU - Ye, Mengchun

PY - 2016/11/2

Y1 - 2016/11/2

N2 - An ortho-selective rhodium-catalyzed direct C−H arylation of 1,1′-bi-2-naphthol (BINOL), to deliver the widely used but not easily available 3,3′-diaryl BINOL, has been developed. This highly efficient one-step synthetic approach is the shortest route to date and is greatly facilitated by the newly developed ligand system comprising tBu2PCl, Ph2-cod, and Cy3P⋅HBF4. In addition, the same procedure can facilitate the challenging syntheses of 3-bulkyaryl BINOLs in good to excellent yields.

AB - An ortho-selective rhodium-catalyzed direct C−H arylation of 1,1′-bi-2-naphthol (BINOL), to deliver the widely used but not easily available 3,3′-diaryl BINOL, has been developed. This highly efficient one-step synthetic approach is the shortest route to date and is greatly facilitated by the newly developed ligand system comprising tBu2PCl, Ph2-cod, and Cy3P⋅HBF4. In addition, the same procedure can facilitate the challenging syntheses of 3-bulkyaryl BINOLs in good to excellent yields.

KW - arylation

KW - biaryls

KW - cross-coupling

KW - ligand design

KW - rhodium

UR - https://www.scopus.com/pages/publications/84991107077

U2 - 10.1002/anie.201607893

DO - 10.1002/anie.201607893

M3 - 文章

AN - SCOPUS:84991107077

SN - 1433-7851

VL - 55

SP - 14116

EP - 14120

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 45

ER -

Ligand-Accelerated Direct C−H Arylation of BINOL: A Rapid One-Step Synthesis of Racemic 3,3′-Diaryl BINOLs

Abstract

Keywords

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