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

^*Corresponding author for this work

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

34 Citations (Scopus)

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
Publication status	Published - May 3 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

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}",

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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

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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

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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