The cobalt-catalyzed cross-dehydrogenative coupling of (benz)oxazoles and ethers is described. Access to some important bioactive heteroaryl ether derivatives was achieved using CoCO as an inexpensive catalyst at levels as low as 1.0 mol %. Investigation of the mechanism indicates a catalytic cycle involving a radical process.
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http://dx.doi.org/10.1021/acs.joc.6b02211 | DOI Listing |
J Org Chem
December 2024
Natural Products and Green Chemistry Division, Central Salt and Marine Chemicals Research Institute (CSIR), G. B. Marg, Bhavnagar 364002, Gujarat, India.
A simple cobalt-catalyzed, picolinamide-directed C8-H sulfoxamination of 1-naphthalamides with NH-sulfoximines has been developed. This cross-dehydrogenative C-H/N-H coupling reaction offers a facile route to N-arylated sulfoximines, exhibiting high yields, a broad substrate scope, and excellent functional group tolerance and scalability.
View Article and Find Full Text PDFJ Org Chem
April 2024
Collaborative Innovation Center for Advanced Organic Chemical Materials Co-constructed by the Province and Ministry, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, P. R. China.
A straight and efficient protocol for the synthesis of hindered indole-ethers via C-H alkoxylation of indoles was developed by a cobalt-catalyzed cross-dehydrogenative coupling reaction with secondary alcohols. The selection of the salicylaldehyde-Co(II) catalyst enables the reaction to proceed under conditions without acid or base addition in the presence of limited alcohols. The protocol has broad substrate scope for both indole and secondary alcohols and exhibits good functional tolerance.
View Article and Find Full Text PDFChem Commun (Camb)
January 2019
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473061, P. R. China.
Cobalt-catalyzed cross-dehydrogenative coupling of N-(2-pyridyl) indoles with free indoles for the construction of unsymmetrical 2,2'-biindoles with excellent regioselectivity is developed. The broader substrate scope as well as the removable directing group of this strategy allows the synthesis of unsymmetrical 2,2'-biindoles to be accessible in organic synthesis.
View Article and Find Full Text PDFJ Org Chem
June 2018
Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province , Xiamen University, Xiamen , Fujian 361005 , China.
The first oxidative C(sp)-H phosphonylation of tertiary aliphatic amines has been developed. The use of cobalt acetate as a catalyst, N-hydroxyphthalimide as a cocatalyst, and air as an oxidant enabled the conversion of tertiary aromatic and aliphatic amines into α-aminophosphonates in moderate to excellent yields under mild conditions via a cross dehydrogenative coupling reaction.
View Article and Find Full Text PDFJ Org Chem
July 2018
College of Chemistry and Molecular Engineering , Zhengzhou University, Zhengzhou , Henan 450001 , China.
Organosulfides have great significance and value in synthetic and biological chemistry. To establish a versatile and green methodology for C-S bond generation, we successfully developed a new aerobic cross-dehydrogenative coupling of C-H and S-H to synthesize aryl sulfides in water, utilizing CoPcS as the catalyst and O as the oxidant. This protocol shows great tolerance of a wide range of substrates.
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