4.4 Review

Research and Application of N-Ts Cyanamides in Organic Synthesis

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Summary: A novel and efficient method for the synthesis of five-membered cyclic guanidines has been developed, which involves a regioselective ring-opening and cyclization process. The reaction proceeds under mild conditions without the need for metals or strong bases. Biologically active urea analogues can also be easily obtained through hydrolysis of the synthesized guanidines.

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Summary: A Ni-catalyzed reductive arylcyanation of alkene using an environmentally benign and nontoxic organo cyanating reagent has been developed. This method allows for the rapid synthesis of cyanosubstituted oxindoles and isoquinoline-1,3-diones with high functional group tolerance, and also features an enantioselective version for the construction of enantiomerically enriched 3-cyanomethyl oxindoles. Additionally, this approach has been successfully applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.

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Summary: A new method for the stereospecific cyanation of olefinic C-H bonds using rhodium catalysis has been developed, resulting in the synthesis of beta,beta-disubstituted acrylonitriles under mild conditions. This approach does not require directing groups, tolerates various functional groups, and provides a concise and green access to a wide range of disubstituted acrylonitriles in good to excellent yields.

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Copper-Catalyzed Regioselective ortho C-H Cyanation of Vinylarenes

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Versatile ruthenium(II)-catalyzed C-H cyanations of benzamides

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Rhodium-Catalyzed Directed C-H Cyanation of Arenes with N-Cyano-N-phenyl-p-toluenesulfonamide

Tian-Jun Gong et al.

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Rhodium Catalyzed Cyanation of Chelation Assisted C-H Bonds

Manthena Chaitanya et al.

ORGANIC LETTERS (2013)

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A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids

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A Novel and Convenient Synthesis of Benzonitriles: Electrophilic Cyanation of Aryl and Heteroaryl Bromides

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