A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) Complexes

Guangrong Meng; Peng Lei; Michal Szostak

doi:https://doi.org/10.1021/acs.orglett.7b00796

A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) Complexes

Guangrong Meng, Peng Lei, Michal Szostak

SASN Chemistry

Rutgers, The State University

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

97 Scopus citations

Abstract

The first general method is reported for transamidation of secondary carboxamides catalyzed by Pd-NHC (NHC = N-heterocyclic carbene) complexes. Commercially available, air- and moisture-stable (NHC)Pd(R-allyl)Cl complexes can effect C-N cross-coupling of a wide range of N-Boc and N-Ts amides, obtained by selective amide N-functionalization, with non-nucleophilic anilines and sterically hindered amines in very good yields. The first use of versatile Pd-NHC complexes as catalysts is represented for transition-metal-catalyzed C(acyl)-N amination of amides by N-C activation.

Original language	English (US)
Pages (from-to)	2158-2161
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.7b00796
State	Published - Apr 21 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) Complexes",

abstract = "The first general method is reported for transamidation of secondary carboxamides catalyzed by Pd-NHC (NHC = N-heterocyclic carbene) complexes. Commercially available, air- and moisture-stable (NHC)Pd(R-allyl)Cl complexes can effect C-N cross-coupling of a wide range of N-Boc and N-Ts amides, obtained by selective amide N-functionalization, with non-nucleophilic anilines and sterically hindered amines in very good yields. The first use of versatile Pd-NHC complexes as catalysts is represented for transition-metal-catalyzed C(acyl)-N amination of amides by N-C activation.",

author = "Guangrong Meng and Peng Lei and Michal Szostak",

note = "Funding Information: Financial support was provided by Rutgers University. The 500 MHz spectrometer used in this study was supported by the NSF-MRI grant (CHE-1229030). P.L. thanks the China Scholarship Council (No. 201606350069) for a fellowship. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "https://doi.org/10.1021/acs.orglett.7b00796",

language = "English (US)",

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T1 - A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) Complexes

AU - Meng, Guangrong

AU - Lei, Peng

AU - Szostak, Michal

N1 - Funding Information: Financial support was provided by Rutgers University. The 500 MHz spectrometer used in this study was supported by the NSF-MRI grant (CHE-1229030). P.L. thanks the China Scholarship Council (No. 201606350069) for a fellowship. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/4/21

Y1 - 2017/4/21

N2 - The first general method is reported for transamidation of secondary carboxamides catalyzed by Pd-NHC (NHC = N-heterocyclic carbene) complexes. Commercially available, air- and moisture-stable (NHC)Pd(R-allyl)Cl complexes can effect C-N cross-coupling of a wide range of N-Boc and N-Ts amides, obtained by selective amide N-functionalization, with non-nucleophilic anilines and sterically hindered amines in very good yields. The first use of versatile Pd-NHC complexes as catalysts is represented for transition-metal-catalyzed C(acyl)-N amination of amides by N-C activation.

AB - The first general method is reported for transamidation of secondary carboxamides catalyzed by Pd-NHC (NHC = N-heterocyclic carbene) complexes. Commercially available, air- and moisture-stable (NHC)Pd(R-allyl)Cl complexes can effect C-N cross-coupling of a wide range of N-Boc and N-Ts amides, obtained by selective amide N-functionalization, with non-nucleophilic anilines and sterically hindered amines in very good yields. The first use of versatile Pd-NHC complexes as catalysts is represented for transition-metal-catalyzed C(acyl)-N amination of amides by N-C activation.

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JO - Organic letters

JF - Organic letters

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A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) Complexes

Abstract

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