International Journal of Organic Chemistry, 2017, 7, 254-262
http://www.scirp.org/journal/ijoc
ISSN Online: 2161-4695
ISSN Print: 2161-4687
DOI: 10.4236/ijoc.2017.73019 Aug. 11, 2017 254 International Journal of Organic Chemistry
Cu-Pd Dual Catalyst System for Amide
Styrylation Reaction from Potassium
Styryltrifluoroborates and Amides
Mohammad Al-Masum
*
, Mohammed Shahidul Islam, Wejdan Shaban
Department of Chemistry, Tennessee State University, Nashville, TN, USA
Abstract
An interesting reaction procedure for the cross-coupling of potassium styryl-
trifluoroborates and amides has been developed by using PdCl
2
(d
t
bpf)-CuI
dual catalyst system. By applying this method, good numbers of amide styry-
lation products are formed in 85% - 92% yields.
Keywords
Amide Styrylation Reaction, Dual Catalyst, Microwave
1. Introduction
Nitrogen containing compounds are important because of their presence in nat-
ural products, their presence in synthetic organic products, and they display
wide-range of functionalities. The formation of the C-N bond is important as it
opens avenues for introducing nitrogen in organic molecules. Buchwald and
Hartwig have separately developed successful metal complexes and ligands for
the construction of C-N bonds using transition metal-catalyst [1]-[7]. Although
significant progress has occurred in this field, the formation of C-N bond
through amide styrylation reaction has not been animated by many chemists.
The pioneering work by Buchwald’s group on palladium-catalyzed intermolecu-
lar amidation of aryl halides and effective use of Xantphos as ligand is promising
[8]. In another development, Buchwald showed the copper-catalyzed amidation
of vinyl halides and the effective use of N,N’-dimethyl ethylene diamine ligand
[9]. Hartwig also reported the ligand effect of P(
t
Bu)
3
and Pd-catalyzed intermo-
lecular cross-coupling of aryl bromides and chlorides with tert-butyl carbamate
[10]. Other groups also reported palladium-catalyzed amide arylation reactions
How to cite this paper: Al-Masum, M.,
Islam, M.S. and Shaban, W. (2017) Cu-Pd
Dual Catalyst System for Amide Styrylation
Reaction from Potassium Styryltrifluorobo-
rates and Amides. International Journal of
Organic Chemistry, 7, 254-262.
https://doi.org/10.4236/ijoc.2017.73019
Received: June 30, 2017
Accepted: August 8, 2017
Published: August 11, 2017
Copyright © 2017 by authors and
Scientific Research Publishing Inc.
This work is licensed under the Creative
Commons Attribution International
License (CC BY 4.0).
http://creativecommons.org/licenses/by/4.0/
Open Access