Pd(II)-catalyzed intermolecular arylation of unactivated C(sp 3)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

Yu Wei; Huarong Tang; Xuefeng Cong; Bin Rao; Chao Wu; Xiaoming Zeng

doi:10.1021/ol500745t

Pd(II)-catalyzed intermolecular arylation of unactivated C(sp ³)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

Yu Wei
, Huarong Tang
, Xuefeng Cong
, Bin Rao
, Chao Wu
, Xiaoming Zeng

Frontier Institute of Science and Technology

Xi'an Jiaotong University

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

91 Scopus citations

Abstract

An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp³)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K₂CO₃ base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp³)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.

Original language	English
Pages (from-to)	2248-2251
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	8
DOIs	https://doi.org/10.1021/ol500745t
State	Published - 18 Apr 2014

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10.1021/ol500745t

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title = "Pd(II)-catalyzed intermolecular arylation of unactivated C(sp 3)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary",

abstract = "An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.",

author = "Yu Wei and Huarong Tang and Xuefeng Cong and Bin Rao and Chao Wu and Xiaoming Zeng",

year = "2014",

month = apr,

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doi = "10.1021/ol500745t",

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TY - JOUR

T1 - Pd(II)-catalyzed intermolecular arylation of unactivated C(sp 3)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

AU - Wei, Yu

AU - Tang, Huarong

AU - Cong, Xuefeng

AU - Rao, Bin

AU - Wu, Chao

AU - Zeng, Xiaoming

PY - 2014/4/18

Y1 - 2014/4/18

N2 - An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.

AB - An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.

UR - https://www.scopus.com/pages/publications/84898940766

U2 - 10.1021/ol500745t

DO - 10.1021/ol500745t

M3 - 文章

AN - SCOPUS:84898940766

SN - 1523-7060

VL - 16

SP - 2248

EP - 2251

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Pd(II)-catalyzed intermolecular arylation of unactivated C(sp ³)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

Abstract

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