Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/73253
Title: Part I. Synthesis of chiral 3-substituted indanones via transition-metal-catalyzed reductive heck reaction. Part II. Tert-butyl peroxybenzoate promoted oxidative coupling between heteroarenes and alkanes
Authors: Lei, Kaining
Keywords: DRNTU::Science
Issue Date: 2018
Publisher: Nanyang Technological University
Source: Lei, K. (2018). Part I. Synthesis of chiral 3-substituted indanones via transition-metal-catalyzed reductive heck reaction. Part II. Tert-butyl peroxybenzoate promoted oxidative coupling between heteroarenes and alkanes. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: A new approach to chiral 3-substituted indanones via palladium-catalyzed reductive Heck reaction with excellent yields (>80%) and enantioselectivities (>90% ee) had been developed. Substrates with ortho-, para- substitution, or with electron-donating, electron-withdrawing groups on the phenyl ring could be tolerated. The ammonium salts, along with ethylene glycol could offer hydrogen-bonding, which help dissociate C-Br bond to promote a cationic pathway. A straightforward synthesis of chiral 3-substituted indanones via nickel-catalyzed reductive Heck reaction with good yields (>60%) and enantioselectivities (60%~80% ee) had been developed. A new strategy for building C-C bond between electron-deficient heteroarenes and cycloalkanes via oxidative coupling was developed. The reaction was promoted by TBPB and went through a radical pathway. No metal catalyst was needed. This method could build a wide range of alkyl heteroarenes which were useful in medicinal chemistry.
URI: http://hdl.handle.net/10356/73253
Rights: This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0).
Fulltext Permission: embargo_restricted_20220731
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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