Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides

Shu Yu Zhang; Gang He; William A. Nack; Yingsheng Zhao; Qiong Li; Gong Chen

doi:10.1021/ja312277g

Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp³)-H bonds with alkyl iodides

Shu Yu Zhang
, Gang He
, William A. Nack
, Yingsheng Zhao
, Qiong Li
, Gong Chen

Chemistry

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

353 Scopus citations

Abstract

We report an efficient method for the alkylation of γ-C(sp ³)-H bonds of picolinamide-protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag₂CO₃ and dibenzyl phosphate, (BnO)₂PO₂H, are critical promoters of this reaction. These reactions provide a convenient and straightforward method for the preparation of high-value N-containing products from readily available amine and alkyl iodide precursors.

Original language	English (US)
Pages (from-to)	2124-2127
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	6
DOIs	https://doi.org/10.1021/ja312277g
State	Published - Feb 13 2013

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja312277g

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abstract = "We report an efficient method for the alkylation of γ-C(sp 3)-H bonds of picolinamide-protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag2CO3 and dibenzyl phosphate, (BnO)2PO2H, are critical promoters of this reaction. These reactions provide a convenient and straightforward method for the preparation of high-value N-containing products from readily available amine and alkyl iodide precursors.",

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T1 - Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp3)-H bonds with alkyl iodides

AU - Zhang, Shu Yu

AU - He, Gang

AU - Nack, William A.

AU - Zhao, Yingsheng

AU - Li, Qiong

AU - Chen, Gong

PY - 2013/2/13

Y1 - 2013/2/13

N2 - We report an efficient method for the alkylation of γ-C(sp 3)-H bonds of picolinamide-protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag2CO3 and dibenzyl phosphate, (BnO)2PO2H, are critical promoters of this reaction. These reactions provide a convenient and straightforward method for the preparation of high-value N-containing products from readily available amine and alkyl iodide precursors.

AB - We report an efficient method for the alkylation of γ-C(sp 3)-H bonds of picolinamide-protected aliphatic amine substrates with primary alkyl iodides via palladium catalysis. Ag2CO3 and dibenzyl phosphate, (BnO)2PO2H, are critical promoters of this reaction. These reactions provide a convenient and straightforward method for the preparation of high-value N-containing products from readily available amine and alkyl iodide precursors.

UR - https://www.scopus.com/pages/publications/84873667624

UR - https://www.scopus.com/pages/publications/84873667624#tab=citedBy

U2 - 10.1021/ja312277g

DO - 10.1021/ja312277g

M3 - Article

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AN - SCOPUS:84873667624

SN - 0002-7863

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 6

ER -

Palladium-catalyzed picolinamide-directed alkylation of unactivated C(sp³)-H bonds with alkyl iodides

Abstract

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