Palladium(II)-Catalyzed Stereospecific Alkenyl C-H Bond Alkylation of Allylamines with Alkyl Iodides

Yun Cheng Luo; Chao Yang; Sheng Qi Qiu; Qiu Ju Liang; Yun He Xu; Teck Peng Loh

doi:10.1021/acscatal.8b04415

Palladium(II)-Catalyzed Stereospecific Alkenyl C-H Bond Alkylation of Allylamines with Alkyl Iodides

Yun Cheng Luo, Chao Yang, Sheng Qi Qiu, Qiu Ju Liang, Yun He Xu, Teck Peng Loh

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

34 Scopus citations

Abstract

A palladium-catalyzed stereospecific alkylation of allylamines with primary and secondary alkyl iodides is described. Isoquinoline-1-carboxamide (IQA) acts as directing group to generate multisubstituted olefin products in cis configuration in moderate to good yields. Mechanistic studies suggest that alkenyl C-H bond activation is the rate-determining step.

Original language	English
Pages (from-to)	4271-4276
Number of pages	6
Journal	ACS Catalysis
Volume	9
Issue number	5
DOIs	https://doi.org/10.1021/acscatal.8b04415
State	Published - 3 May 2019
Externally published	Yes

Keywords

alkenyl C-H activation
alkylation
bidentate directing group
palladium
stereospecific

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10.1021/acscatal.8b04415

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title = "Palladium(II)-Catalyzed Stereospecific Alkenyl C-H Bond Alkylation of Allylamines with Alkyl Iodides",

abstract = "A palladium-catalyzed stereospecific alkylation of allylamines with primary and secondary alkyl iodides is described. Isoquinoline-1-carboxamide (IQA) acts as directing group to generate multisubstituted olefin products in cis configuration in moderate to good yields. Mechanistic studies suggest that alkenyl C-H bond activation is the rate-determining step.",

keywords = "alkenyl C-H activation, alkylation, bidentate directing group, palladium, stereospecific",

author = "Luo, {Yun Cheng} and Chao Yang and Qiu, {Sheng Qi} and Liang, {Qiu Ju} and Xu, {Yun He} and Loh, {Teck Peng}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = may,

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doi = "10.1021/acscatal.8b04415",

language = "英语",

volume = "9",

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T1 - Palladium(II)-Catalyzed Stereospecific Alkenyl C-H Bond Alkylation of Allylamines with Alkyl Iodides

AU - Luo, Yun Cheng

AU - Yang, Chao

AU - Qiu, Sheng Qi

AU - Liang, Qiu Ju

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2019/5/3

Y1 - 2019/5/3

N2 - A palladium-catalyzed stereospecific alkylation of allylamines with primary and secondary alkyl iodides is described. Isoquinoline-1-carboxamide (IQA) acts as directing group to generate multisubstituted olefin products in cis configuration in moderate to good yields. Mechanistic studies suggest that alkenyl C-H bond activation is the rate-determining step.

AB - A palladium-catalyzed stereospecific alkylation of allylamines with primary and secondary alkyl iodides is described. Isoquinoline-1-carboxamide (IQA) acts as directing group to generate multisubstituted olefin products in cis configuration in moderate to good yields. Mechanistic studies suggest that alkenyl C-H bond activation is the rate-determining step.

KW - alkenyl C-H activation

KW - alkylation

KW - bidentate directing group

KW - palladium

KW - stereospecific

UR - http://www.scopus.com/inward/record.url?scp=85064980598&partnerID=8YFLogxK

U2 - 10.1021/acscatal.8b04415

DO - 10.1021/acscatal.8b04415

M3 - 文章

AN - SCOPUS:85064980598

SN - 2155-5435

VL - 9

SP - 4271

EP - 4276

JO - ACS Catalysis

JF - ACS Catalysis

IS - 5

ER -

Palladium(II)-Catalyzed Stereospecific Alkenyl C-H Bond Alkylation of Allylamines with Alkyl Iodides

Abstract

Keywords

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