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^*

^*Corresponding author for this work

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

53 Scopus citations

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.

Original language	English
Pages (from-to)	16080-16083
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	45
DOIs	https://doi.org/10.1021/jacs.7b09761
State	Published - 15 Nov 2017
Externally published	Yes

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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",

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doi = "10.1021/jacs.7b09761",

language = "英语",

volume = "139",

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journal = "Journal of the American Chemical Society",

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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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