SHERP

Transition Metal-Catalyzed Oxygenative α-Addition and β-Alkylation of Terminal Alkynes
전이금속 촉매 하에 말단 알카인의 산화적 α–첨가 및 β–알킬화 반응

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Authors
윤희경
Advisor
이철범
Major
자연과학대학 화학부
Issue Date
2017
Publisher
서울대학교 대학원
Keywords
Disubstituted rhodium vinylideneMetalloketeneβ-AlkylationOxygenative α-addition5-Membered ring synthesisCarbonyl synthesis
Description
학위논문 (석사)-- 서울대학교 대학원 : 화학부, 2017. 2. 이철범.
Abstract
Described in this dissertation is the development of the transition metal-catalyzed cyclization and oxygenative nucleophilic addition of terminal alkynes which gives cyclopentane and cyclohexane carboxylic acid derivatives as products. Using terminal alkynes tethered with electrophiles such as alkyl halides, aldehydes, imines, and Michael acceptors, the reaction can be carried out with a broad range of nucleophiles such as alcohols and amines in the presence of a suitable base, oxidant and rhodium catalyst. The proposed mechanism involves the formation of a disubstituted metal vinylidene intermediate via β-alkylation followed by transfer oxygenation to form a metalloketene which then undergoes nucleophilic addition. This transformation can provide diverse ester and amide products while forming a 5- and 6-membered ring moiety.
Language
English
URI
http://hdl.handle.net/10371/134947
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College of Humanities (인문대학)Korean Language and Literature (국어국문학과)Others_국어국문학과
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