Construction of Axial Chirality by Rhodium-Catalyzed Asymmetric Dehydrogenative Heck Coupling of Biaryl Compounds with Alkenes

• Published in: Angewandte Chemie International Edition Vol. 53; no. 48; pp. 13244 - 13247
• Main Authors: Zheng, Jun, You, Shu-Li
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 24-11-2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alkenes; Alkenes - chemistry; asymmetric catalysis; Asymmetry; biaryls; Bonding; Catalysis; Catalysts; Chirality; Conjugates; Construction; Cyclization; CH activation; Joining; Ligands; Models, Molecular; rhodium; Rhodium - chemistry; Stereoisomerism; CH activation; asymmetric catalysis; biaryls; chirality; rhodium
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201408805

Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate additions.
An axe to grind? Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst (1), in good to excellent yields and enantioselectivities. The biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate addition reactions.