Palladium-catalyzed ligand-promoted site-selective cyanomethylation of unactivated C(sp3)–H bonds with acetonitrile†
†Electronic supplementary information (ESI) available: Experimental details including characterization data, copies of 1H, 13C NMR and NOESY spectra. See DOI: 10.1039/c5sc04066c
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Abstract

The direct coupling of unactivated sp ³ C–H bonds in aliphatic amides with acetonitrile was achieved via palladium catalysis.

Abstract

The direct cyanomethylation of unactivated sp ³ C–H bonds of aliphatic amides was achieved via palladium catalysis assisted by a bidentate directing group with good functional group compatibility. This process represents the first example of the direct cross-coupling of sp ³ C–H bonds with acetonitrile. Considering the importance of the cyano group in medicinal and synthetic organic chemistry, this reaction will find broad application in chemical research.

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Most cited references 13

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Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

Darcy A Culkin, John F Hartwig (2003)

The palladium-catalyzed alpha-arylation of ketones has become a useful and general synthetic method. In this process, an enolate is generated from a ketone and base in the presence of an aryl halide, and a palladium catalyst couples this enolate with the aryl halide. With the advent of new catalysts composed of sterically hindered, electron-rich alkylphosphine and N-heterocyclic carbene ligands, this process now encompasses a broad range of enolates and related anions, including those derived from amides, esters, aldehydes, nitriles, malonates, cyanoesters, nitroalkanes, sulfones, and lactones. In the proposed mechanism for this reaction, the carbon-carbon bond of the product is formed by reductive elimination from an arylpalladium enolate intermediate. The structures and reactions of arylpalladium complexes of enolate, cyanoalkyl, and malonate ions have been studied to determine how the binding mode and electronic and steric parameters influence the rate and mechanism of reductive elimination.

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Author and article information

Journal

Journal ID (nlm-ta): Chem Sci

Journal ID (iso-abbrev): Chem Sci

Title: Chemical Science

Publisher: Royal Society of Chemistry

ISSN (Print): 2041-6520

ISSN (Electronic): 2041-6539

Publication date (Print): 21 April 2016

Publication date (Electronic): 06 January 2016

Volume: 7

Issue: 4

Pages: 2804-2808

Affiliations

[a ] Department of Chemistry and Chemical Biology , Indiana University-Purdue University Indianapolis , Indianapolis , Indiana 46202 , USA . Email: geh@ 123456iupui.edu

[b ] Institute of Chemistry and BioMedical Sciences , School of Chemistry and Chemical Engineering , Nanjing University , Nanjing 210093 , P. R. China

Article

Publisher ID: c5sc04066c

DOI: 10.1039/c5sc04066c

PMC ID: 5477045

SO-VID: a5e7589a-a086-4eb9-8824-2b1ecff6372d

License:

This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License ( http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

History

Date received : 26 October 2015

Date accepted : 6 January 2016

Notes

†Electronic supplementary information (ESI) available: Experimental details including characterization data, copies of ¹H, ¹³C NMR and NOESY spectra. See DOI: 10.1039/c5sc04066c

Data availability:

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