Ruthenium- and Rhodium-Catalyzed Strain-Driven Cleavage and Reconstruction of the C-C Bond

• Published in: European journal of organic chemistry Vol. 2016; no. 7; pp. 1232 - 1242
• Main Author: Kondo, Teruyuki
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.03.2016; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Chemical bonds; Cleavage reactions; Homogenous catalysis; Rhodium; Ruthenium; Strained molecules
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201501291

The synthesis of new functional organic molecules that cannot be obtained by a simple combination of conventional synthetic methods is a challenging subject in organic, organometallic, and industrial chemistry as well as in atom‐efficient and environmental organic synthesis. Among the various possibilities that have been considered, the catalytic cleavage and reconstruction of the C–C bond has opened the door to a new branch of synthetic organic chemistry. This microreview summarizes progress on the ruthenium‐ and rhodium‐catalyzed strain‐driven cleavage of the C–C bond, the methods of which were mostly developed by the author. The direct oxidative addition of 2,5‐norbornadienes, cyclopropenones, cyclobutenones, and cyclobutenediones, and to catalytically active metal species followed by the construction of the C–C bond has been used for the preparation of new organic molecules. Over the last three decades, significant progress has been made towards homogeneous catalytic cleavage and the reconstruction of the C–C bond for fine chemical synthesis. This microreview summarizes the ruthenium‐ and rhodium‐catalyzed strain‐driven cleavage and reconstruction of the C–C bond, which gives new functional organic molecules that cannot be obtained by conventional synthetic methods.