Free Amino Group-Directed ?-C(sp3)-H Arylation of α-Amino Esters with Diaryliodonium Triflates by Palladium Catalysis

Pranab K. Pramanick; Zhibing Zhou; Zhen Lin Hou; Bo Yao

doi:10.1021/acs.joc.9b00605

Free Amino Group-Directed ?-C(sp³)-H Arylation of α-Amino Esters with Diaryliodonium Triflates by Palladium Catalysis

Pranab K. Pramanick
, Zhibing Zhou
, Zhen Lin Hou
, Bo Yao^*

^*Corresponding author for this work

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

37 Citations (Scopus)

Abstract

Free amino group-directed C(sp³)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH₂-directed C(sp³)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag₂O as the additive, we developed the first NH₂-directed ?-C(sp³)-H arylation of α-amino esters with diaryliodonium triflates for the construction of synthetically useful ?-aryl-α-amino esters, and the result of the KIE study suggested that the catalytic reaction involved an irreversible C-H cleavage as the rate-determining step.

Original language	English
Pages (from-to)	5684-5694
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	84
Issue number	9
DOIs	https://doi.org/10.1021/acs.joc.9b00605
Publication status	Published - 3 May 2019
Externally published	Yes

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abstract = "Free amino group-directed C(sp3)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH2-directed C(sp3)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag2O as the additive, we developed the first NH2-directed ?-C(sp3)-H arylation of α-amino esters with diaryliodonium triflates for the construction of synthetically useful ?-aryl-α-amino esters, and the result of the KIE study suggested that the catalytic reaction involved an irreversible C-H cleavage as the rate-determining step.",

author = "Pramanick, \{Pranab K.\} and Zhibing Zhou and Hou, \{Zhen Lin\} and Bo Yao",

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

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AU - Pramanick, Pranab K.

AU - Zhou, Zhibing

AU - Hou, Zhen Lin

AU - Yao, Bo

PY - 2019/5/3

Y1 - 2019/5/3

N2 - Free amino group-directed C(sp3)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH2-directed C(sp3)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag2O as the additive, we developed the first NH2-directed ?-C(sp3)-H arylation of α-amino esters with diaryliodonium triflates for the construction of synthetically useful ?-aryl-α-amino esters, and the result of the KIE study suggested that the catalytic reaction involved an irreversible C-H cleavage as the rate-determining step.

AB - Free amino group-directed C(sp3)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH2-directed C(sp3)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag2O as the additive, we developed the first NH2-directed ?-C(sp3)-H arylation of α-amino esters with diaryliodonium triflates for the construction of synthetically useful ?-aryl-α-amino esters, and the result of the KIE study suggested that the catalytic reaction involved an irreversible C-H cleavage as the rate-determining step.

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Free Amino Group-Directed ?-C(sp³)-H Arylation of α-Amino Esters with Diaryliodonium Triflates by Palladium Catalysis

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