Co-reporter:Zhen Zhang, Fan Xiao, Baoliang Huang, Jincheng Hu, Bin Fu, and Zhenhua Zhang
Organic Letters 2016 Volume 18(Issue 5) pp:908-911
Publication Date(Web):February 23, 2016
DOI:10.1021/acs.orglett.5b03570
A self-relay rhodium(I)-catalyzed cyclization of alkyne–azides with two σ-donor/π-acceptor ligands (isonitriles and CO) to form sequentially multiple-fused heterocycle systems via tandem nitrene transformation and aza-Pauson–Khand cyclization has been developed. In this approach, an intriguing chemoselective insertion process of isonitriles superior to CO was observed. This reaction provides an alternative strategy to synthesize functionalized pyrrolo[2,3-b]indole scaffolds.
Co-reporter:Jin Zhao, Zongyang Li, Shuaihu Yan, Shiyang Xu, Ming-An Wang, Bin Fu, and Zhenhua Zhang
Organic Letters 2016 Volume 18(Issue 8) pp:1736-1739
Publication Date(Web):March 25, 2016
DOI:10.1021/acs.orglett.6b00381
A facile and efficient Pd/C-catalyzed carbonylation of both aliphatic and aromatic azides in the presence of amines is reported. Serving as the widely existed fragments in an array of biological pharmaceuticals, functionalized unsymmetrical ureas were straightforwardly synthesized by using readily available and cheap azides with amines under CO atmosphere, with the extrusion of N2 as the only byproduct. It was found that not only aryl azides but also benzyl and alkyl azides were suited for this methodology. Another feature of this procedure was the employment of a highly efficient palladium charcoal catalytic system.
Co-reporter:Jin Zhao;Zongyang Li;Shaole Song;Dr. Ming-An Wang;Dr. Bin Fu ;Dr. Zhenhua Zhang
Angewandte Chemie International Edition 2016 Volume 55( Issue 18) pp:5545-5549
Publication Date(Web):
DOI:10.1002/anie.201600887
Abstract
A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.
Co-reporter:Jin Zhao;Zongyang Li;Shaole Song;Dr. Ming-An Wang;Dr. Bin Fu ;Dr. Zhenhua Zhang
Angewandte Chemie 2016 Volume 128( Issue 18) pp:5635-5639
Publication Date(Web):
DOI:10.1002/ange.201600887
Abstract
A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.
Co-reporter:Zhen Zhang, Zongyang Li, Bin Fu and Zhenhua Zhang
Chemical Communications 2015 vol. 51(Issue 91) pp:16312-16315
Publication Date(Web):18 Sep 2015
DOI:10.1039/C5CC05981J
An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.
Co-reporter:Zhen Zhang, Zongyang Li, Bin Fu and Zhenhua Zhang
Chemical Communications 2015 - vol. 51(Issue 91) pp:NaN16315-16315
Publication Date(Web):2015/09/18
DOI:10.1039/C5CC05981J
An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.