Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation

Ru Yi Zhu; Luo Yan Liu; Han Seul Park; Kai Hong; Yongwei Wu; Chris H. Senanayake; Jin Quan Yu

doi:10.1021/jacs.7b09761

Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp³)-H Activation

Ru Yi Zhu
, Luo Yan Liu
, Han Seul Park
, Kai Hong
, Yongwei Wu
, Chris H. Senanayake
, Jin Quan Yu^*

^*此作品的通讯作者

Scripps Research Institute
Boehringer Ingelheim GmbH

科研成果: 期刊稿件 › 文章 › 同行评审

54 引用（Scopus）

摘要

We report Pd(II)-catalyzed β-C(sp³)-H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported β-C(sp³)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl coupling involving both primary and secondary alkyls.

源语言	英语
页（从-至）	16080-16083
页数	4
期刊	Journal of the American Chemical Society
卷	139
期	45
DOI	https://doi.org/10.1021/jacs.7b09761
出版状态	已出版 - 15 11月 2017
已对外发布	是

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title = "Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation",

abstract = "We report Pd(II)-catalyzed β-C(sp3)-H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported β-C(sp3)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl coupling involving both primary and secondary alkyls.",

author = "Zhu, \{Ru Yi\} and Liu, \{Luo Yan\} and Park, \{Han Seul\} and Kai Hong and Yongwei Wu and Senanayake, \{Chris H.\} and Yu, \{Jin Quan\}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = nov,

day = "15",

doi = "10.1021/jacs.7b09761",

language = "英语",

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T1 - Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation

AU - Zhu, Ru Yi

AU - Liu, Luo Yan

AU - Park, Han Seul

AU - Hong, Kai

AU - Wu, Yongwei

AU - Senanayake, Chris H.

AU - Yu, Jin Quan

PY - 2017/11/15

Y1 - 2017/11/15

N2 - We report Pd(II)-catalyzed β-C(sp3)-H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported β-C(sp3)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl coupling involving both primary and secondary alkyls.

AB - We report Pd(II)-catalyzed β-C(sp3)-H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported β-C(sp3)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl coupling involving both primary and secondary alkyls.

UR - https://www.scopus.com/pages/publications/85034220264

U2 - 10.1021/jacs.7b09761

DO - 10.1021/jacs.7b09761

M3 - 文章

C2 - 29086554

AN - SCOPUS:85034220264

SN - 0002-7863

VL - 139

SP - 16080

EP - 16083

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 45

ER -

Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation

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Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp³)-H Activation