An efficient synthesis of isoindolin-1-ones from oxalyl amide-protected benzylamines, through ruthenium-catalyzed intramolecular C(sp)-H carbonylation, has been developed. Variously substituted benzylamines could be well tolerated in this new protocol, affording the corresponding products in moderate to excellent yields. This approach constitutes the first example of Ru(II)-catalyzed C(sp)-H carbonylation with isocyanate as a novel commercially available carbonyl source.
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Ruthenium-Catalyzed Carbonylation of Oxalyl Amide-Protected Benzylamines with Isocyanate as the Carbonyl Source.
J Org Chem
July 2017
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
An efficient synthesis of isoindolin-1-ones from oxalyl amide-protected benzylamines, through ruthenium-catalyzed intramolecular C(sp)-H carbonylation, has been developed. Variously substituted benzylamines could be well tolerated in this new protocol, affording the corresponding products in moderate to excellent yields. This approach constitutes the first example of Ru(II)-catalyzed C(sp)-H carbonylation with isocyanate as a novel commercially available carbonyl source.
View Article and Find Full Text PDFRhodium(III)-Catalyzed Oxidative C-H/C-H Cross-Coupling of Heteroarenes and Masked Benzylamines.
Org Lett
December 2016
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
The first example of oxidative C-H/C-H cross-coupling of oxalyl amide-protected benzylamines and various heteroarenes in the presence of a rhodium(III) catalyst has been developed. The route provides a means of synthesizing ortho-heteroarylated benzylamines. The methodology presents broad substrate scope, great functional group tolerance, and good to excellent yields in the synthesis of substituted benzylamines.
View Article and Find Full Text PDFPd-Catalyzed Coupling of γ-C(sp(3))-H Bonds of Oxalyl Amide-Protected Amino Acids with Heteroaryl and Aryl Iodides.
J Org Chem
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Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Pd-catalyzed regioselective coupling of γ-C(sp(3))-H bonds of oxalyl amide-protected amino acids with heteroaryl and aryl iodides is reported. A wide variety of iodides are tolerated, giving the corresponding products in moderate to good yields. Various oxalyl amide-protected amino acids were compatible in this C-H transformation, thus representing a practical method for constructing non-natural amino acid derivatives.
View Article and Find Full Text PDFHighly regioselective meta arylation of oxalyl amide-protected β-arylethylamine via the Catellani reaction.
Chem Commun (Camb)
May 2016
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.
The first bidentate directing group assisted highly selective meta arylation of β-arylethylamine derivatives via palladium/norbornene catalysis is reported, and the range of aryl iodides for the oxalyl amide assisted meta-selective arylation reactions is broadest yet reported. This meta arylation also proceeds well with thiophene derivatives, giving the corresponding products in satisfactory yields. And three-step functionalization of arylethyloxalamide with three different functional groups is successfully performed.
View Article and Find Full Text PDFOxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones carbonylation of γ-C(sp)-H bonds of aliphatic amine substrates.
Chem Sci
August 2015
Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry , Chemical Engineering and Materials Science Soochow University, Suzhou 215123 , PR China . Email:
The first Pd-catalyzed regioselective γ-carbonylation of oxalyl amide protected aliphatic amines with carbon monoxide leading to synthesis of pyrrolidones has been developed. Both γ-methyl and cyclopropyl methylene C-H bonds are well activated to obtain the corresponding pyrrolidones in moderate to excellent yields. The role of 3-(trifluoromethyl)benzoic acid as an additive is critical as it helps in stabilizing the palladium intermediate formed during the catalytic cycle.
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