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학술지 One-Pot, Regioselective Consecutive Multihalogenation of 2,2'-Bithiophene
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저자
김보람, 김은정, 성기현, 김점종, 신동수, 이상경, 윤용진
발행일
201305
출처
European Journal of Organic Chemistry, v.2013 no.14, pp.2788-2797
ISSN
1434-193X
DOI
https://dx.doi.org/10.1002/ejoc.201300379
협약과제
13ZC1200, 그린IT 융.복합 기술개발, 이수인
초록
The one-pot regioselective consecutive multihalogenation of 2,2??-bithiophene (1) was demonstrated. Compound 1 was consecutively halogenated with lithium halides such as lithium bromide, chloride, and/or iodide in the presence of lead tetraacetate in chloroform at room temperature or under reflux conditions to give 5-bromo(or chloro)-5??-iodo(or chloro)-, 3-bromo(or chloro)-5,5??-dibromo(or dichloro, diiodo)-, 3,3??-dibromo-(or dichloro)-5,5??-diiodo(or dibromo, dichloro)-, and 3,3??,5-tribromo(or trichloro)-5??-iodo(or bromo)-2,2??- bithiophenes. Notably, this process offers a regioselective method for consecutive multihalogenation in one pot, and the yields and selectivity are also higher than those obtained in the step-by-step and concurrent halogenation methods. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
키워드
Electrophilic substitution, Halogenation, Regioselectivity, Sulfur heterocycles, Synthetic methods
KSP 제안 키워드
Co. KGaA, Lithium bromide, One-pot, Room-temperature, Step-by-step, Sulfur heterocycles, Synthetic methods, electrophilic substitution