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One‐Pot, Regioselective Consecutive Multihalogenation of 2,2′‐Bithiophene
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- Authors
- Bo Ram Kim, Eun Jung Kim, Gi Hyeon Sung, Jeum-Jong Kim, Dong-Soo Shin, Sang-Gyeong Lee, Yong-Jin Yoon
- Issue Date
- 2013-05
- Citation
- European Journal of Organic Chemistry, v.2013, no.14, pp.2788-2797
- ISSN
- 1434-193X
- Language
- English
- Type
- Journal Article
- Abstract
- 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.
- KSP Keywords
- Co. KGaA, Lithium bromide, Room temperature, Step-by-step, one-pot