Palladium-catalyzed alkenylation and alkynylation of ortho-C(sp 2)-H bonds of benzylamine picolinamides

Yingsheng Zhao; Gang He; William A. Nack; Gong Chen

doi:10.1021/ol301214u

Palladium-catalyzed alkenylation and alkynylation of ortho-C(sp ²)-H bonds of benzylamine picolinamides

Yingsheng Zhao, Gang He, William A. Nack, Gong Chen

Chemistry

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

90 Scopus citations

Abstract

An efficient functionalization of ortho-C(sp ²)-H bonds of picolinamide (PA)-protected benzylamine substrates with a range of vinyl iodides as well as acetylenic bromide is reported. ortho-Phenyl benzoic acid (oPBA) acts as an effective promoter in this reaction system. This method provides a practical strategy to access highly functionalized benzylamine compounds for organic synthesis.

Original language	English (US)
Pages (from-to)	2948-2951
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	12
DOIs	https://doi.org/10.1021/ol301214u
State	Published - Jun 15 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol301214u

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title = "Palladium-catalyzed alkenylation and alkynylation of ortho-C(sp 2)-H bonds of benzylamine picolinamides",

abstract = "An efficient functionalization of ortho-C(sp 2)-H bonds of picolinamide (PA)-protected benzylamine substrates with a range of vinyl iodides as well as acetylenic bromide is reported. ortho-Phenyl benzoic acid (oPBA) acts as an effective promoter in this reaction system. This method provides a practical strategy to access highly functionalized benzylamine compounds for organic synthesis.",

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AU - Zhao, Yingsheng

AU - He, Gang

AU - Nack, William A.

AU - Chen, Gong

PY - 2012/6/15

Y1 - 2012/6/15

N2 - An efficient functionalization of ortho-C(sp 2)-H bonds of picolinamide (PA)-protected benzylamine substrates with a range of vinyl iodides as well as acetylenic bromide is reported. ortho-Phenyl benzoic acid (oPBA) acts as an effective promoter in this reaction system. This method provides a practical strategy to access highly functionalized benzylamine compounds for organic synthesis.

AB - An efficient functionalization of ortho-C(sp 2)-H bonds of picolinamide (PA)-protected benzylamine substrates with a range of vinyl iodides as well as acetylenic bromide is reported. ortho-Phenyl benzoic acid (oPBA) acts as an effective promoter in this reaction system. This method provides a practical strategy to access highly functionalized benzylamine compounds for organic synthesis.

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Palladium-catalyzed alkenylation and alkynylation of ortho-C(sp ²)-H bonds of benzylamine picolinamides

Abstract

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