Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates

Chengxi Lu; Shu Yu Zhang; Gang He; William A. Nack; Gong Chen

doi:10.1016/j.tet.2014.02.070

Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates

Chengxi Lu
, Shu Yu Zhang
, Gang He
, William A. Nack
, Gong Chen

Chemistry

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

45 Scopus citations

Abstract

We report a new set of methods for the halogenation of the ortho C-H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na)XO₃ and K ₂S₂O₈ reagents, which enables the installation of iodo, bromo, and chloro groups onto the ortho position of N-benzyl picolinamides in a unified fashion. A variety of benzylamine products bearing complex halogen substitution can be quickly prepared from much simpler precursors in good yield and selectivity.

Original language	English (US)
Pages (from-to)	4197-4203
Number of pages	7
Journal	Tetrahedron
Volume	70
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2014.02.070
State	Published - Jul 8 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.02.070

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title = "Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates",

abstract = "We report a new set of methods for the halogenation of the ortho C-H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na)XO3 and K 2S2O8 reagents, which enables the installation of iodo, bromo, and chloro groups onto the ortho position of N-benzyl picolinamides in a unified fashion. A variety of benzylamine products bearing complex halogen substitution can be quickly prepared from much simpler precursors in good yield and selectivity.",

author = "Chengxi Lu and Zhang, \{Shu Yu\} and Gang He and Nack, \{William A.\} and Gong Chen",

note = "Funding Information: We gratefully thank The Pennsylvania State University and the NSF ( CAREER CHE-1055795 ) for financial support of this work. G.C. is an Amgen Young Investigator. ",

year = "2014",

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doi = "10.1016/j.tet.2014.02.070",

language = "English (US)",

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TY - JOUR

T1 - Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates

AU - Lu, Chengxi

AU - Zhang, Shu Yu

AU - He, Gang

AU - Nack, William A.

AU - Chen, Gong

N1 - Funding Information: We gratefully thank The Pennsylvania State University and the NSF ( CAREER CHE-1055795 ) for financial support of this work. G.C. is an Amgen Young Investigator.

PY - 2014/7/8

Y1 - 2014/7/8

N2 - We report a new set of methods for the halogenation of the ortho C-H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na)XO3 and K 2S2O8 reagents, which enables the installation of iodo, bromo, and chloro groups onto the ortho position of N-benzyl picolinamides in a unified fashion. A variety of benzylamine products bearing complex halogen substitution can be quickly prepared from much simpler precursors in good yield and selectivity.

AB - We report a new set of methods for the halogenation of the ortho C-H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na)XO3 and K 2S2O8 reagents, which enables the installation of iodo, bromo, and chloro groups onto the ortho position of N-benzyl picolinamides in a unified fashion. A variety of benzylamine products bearing complex halogen substitution can be quickly prepared from much simpler precursors in good yield and selectivity.

UR - https://www.scopus.com/pages/publications/84901289690

UR - https://www.scopus.com/pages/publications/84901289690#tab=citedBy

U2 - 10.1016/j.tet.2014.02.070

DO - 10.1016/j.tet.2014.02.070

M3 - Article

AN - SCOPUS:84901289690

SN - 0040-4020

VL - 70

SP - 4197

EP - 4203

JO - Tetrahedron

JF - Tetrahedron

IS - 27-28

ER -

Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates

Abstract

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