Palladium-catalyzed oxidative acylation of N-benzyltriflamides with aldehydes via C-H bond activation

Satyasheel Sharma; Jihye Park; Eonjeong Park; Aejin Kim; Minyoung Kim; Jong Hwan Kwak; Young Hoon Jung; In Su Kim

doi:10.1002/adsc.201200889

Palladium-catalyzed oxidative acylation of N-benzyltriflamides with aldehydes via C-H bond activation

Satyasheel Sharma
, Jihye Park
, Eonjeong Park
, Aejin Kim
, Minyoung Kim
, Jong Hwan Kwak
, Young Hoon Jung
, In Su Kim

Department of Pharmacy

Sungkyunkwan University

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

62 Scopus citations

Abstract

A palladium-catalyzed ortho-acylation of N-benzyltriflamides with aldehydes via direct sp² C-H bond activation is described. Benzylamines with a triflamide directing group in the presence of palladium acetate, acetic acid, and tert-butyl hydroperoxide as an oxidant can be effectively coupled with aryl and alkyl aldehydes to provide ortho-acyl-N-benzyltriflamides with a high regioselectivity.

Original language	English
Pages (from-to)	332-336
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	355
Issue number	2-3
DOIs	https://doi.org/10.1002/adsc.201200889
State	Published - 11 Feb 2013

Keywords

Acylation
C-H activation
Catalysis
N-benzyltriflamides
Palladium

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10.1002/adsc.201200889

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title = "Palladium-catalyzed oxidative acylation of N-benzyltriflamides with aldehydes via C-H bond activation",

abstract = "A palladium-catalyzed ortho-acylation of N-benzyltriflamides with aldehydes via direct sp2 C-H bond activation is described. Benzylamines with a triflamide directing group in the presence of palladium acetate, acetic acid, and tert-butyl hydroperoxide as an oxidant can be effectively coupled with aryl and alkyl aldehydes to provide ortho-acyl-N-benzyltriflamides with a high regioselectivity.",

keywords = "Acylation, C-H activation, Catalysis, N-benzyltriflamides, Palladium",

author = "Satyasheel Sharma and Jihye Park and Eonjeong Park and Aejin Kim and Minyoung Kim and Kwak, \{Jong Hwan\} and Jung, \{Young Hoon\} and Kim, \{In Su\}",

year = "2013",

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doi = "10.1002/adsc.201200889",

language = "English",

volume = "355",

pages = "332--336",

journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Palladium-catalyzed oxidative acylation of N-benzyltriflamides with aldehydes via C-H bond activation

AU - Sharma, Satyasheel

AU - Park, Jihye

AU - Park, Eonjeong

AU - Kim, Aejin

AU - Kim, Minyoung

AU - Kwak, Jong Hwan

AU - Jung, Young Hoon

AU - Kim, In Su

PY - 2013/2/11

Y1 - 2013/2/11

N2 - A palladium-catalyzed ortho-acylation of N-benzyltriflamides with aldehydes via direct sp2 C-H bond activation is described. Benzylamines with a triflamide directing group in the presence of palladium acetate, acetic acid, and tert-butyl hydroperoxide as an oxidant can be effectively coupled with aryl and alkyl aldehydes to provide ortho-acyl-N-benzyltriflamides with a high regioselectivity.

AB - A palladium-catalyzed ortho-acylation of N-benzyltriflamides with aldehydes via direct sp2 C-H bond activation is described. Benzylamines with a triflamide directing group in the presence of palladium acetate, acetic acid, and tert-butyl hydroperoxide as an oxidant can be effectively coupled with aryl and alkyl aldehydes to provide ortho-acyl-N-benzyltriflamides with a high regioselectivity.

KW - Acylation

KW - C-H activation

KW - Catalysis

KW - N-benzyltriflamides

KW - Palladium

UR - https://www.scopus.com/pages/publications/84874687519

U2 - 10.1002/adsc.201200889

DO - 10.1002/adsc.201200889

M3 - Article

AN - SCOPUS:84874687519

SN - 1615-4150

VL - 355

SP - 332

EP - 336

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 2-3

ER -

Palladium-catalyzed oxidative acylation of N-benzyltriflamides with aldehydes via C-H bond activation

Abstract

Keywords

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