Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/171844
Title: COBALT-CATALYZED HYDROFUNCTIONALIZATION/CYCLIZATION OF UNSATURATED HYDROCARBONS
Authors: WU CAIZHI
Keywords: cobalt, phosphine ligand, hydrosilylation, hydroboration, cyclization
Issue Date: 20-Jan-2020
Citation: WU CAIZHI (2020-01-20). COBALT-CATALYZED HYDROFUNCTIONALIZATION/CYCLIZATION OF UNSATURATED HYDROCARBONS. ScholarBank@NUS Repository.
Abstract: Our research focused on cobalt catalyzed hydrofunctionlization/cyclization transformations of unsaturated hydrocarbons. Firstly, we reported that cobalt catalysts in combination with phosphine ligands showed good reactivity in hydrosilylation of terminal alkynes with high regio- and stereoselectivity. Additionally, excellent chemoselectivity to alkyne was also observed when double bond and triple bond are in the same substrate. Unlike cobalt pincer complexes, our cobalt/phosphine catalytic system can be in stu activated by silanes without any external activators. Then we made a study of internal allene hydroboration. Our studies strongly suggest the mechanism predominantly favors Co-Bpin intermediate. With the knowledge of cobalt catalyst in promoting hydrofunctionalization of unsaturated hydrocarbons, we extend the catalytic system to hydroboration/cyclization of 1,7-enynes, constructing chiral cyclic compounds. To our delight, a series of chiral quinolinones containing quaternary stereogenic centers at 3-carbon were obtained. The borylated quinolines can be readily converted into a variety of compounds with chiral six-member ring structure.
URI: https://scholarbank.nus.edu.sg/handle/10635/171844
Appears in Collections:Ph.D Theses (Open)

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