Part I: Desymmetrization of cyclic olefins via asymmetric Heck reaction and hydroarylation. Part II: Fast Suzuki coupling of aryl tosylates

• Main Author: Liu, Sijia
• Other Authors: Steve Zhou
• Format: Theses and Dissertations
• Language: English
• Published: 2014
• Subjects: DRNTU::Science::Chemistry
• Online Access: https://hdl.handle.net/10356/55382
• Institution: Nanyang Technological University

Part 1. Asymmetric Heck reaction of substituted cyclopentenes gave one stereoisomer in excellent enantio- and diastereoselectivities. The high selectivity as unprecedented in Heck reaction. (R)-Xyl-SDP(O) was uniquely effective as chiral ligand. Various aryl triflates can be used. The same catalyst can be applied to asymmetric hydroarylation of norbornene and other bicyclic derivatives in excellent ee. Part 2. A general procedure for fast Suzuki coupling of heteroaryl tosylates as developed. Most major families of heteroaryls can couple at room temperature. The method is generally applicable to major families of heterocyclic substrates, and most reactions completed within minutes to hours.