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One‐Pot, Regioselective Consecutive Multihalogenation of 2,2′‐Bithiophene
Author(s) -
Kim Bo Ram,
Kim Eun Jung,
Sung Gi Hyeon,
Kim JeumJong,
Shin DongSoo,
Lee SangGyeong,
Yoon YongJin
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300379
Subject(s) - regioselectivity , chemistry , halogenation , iodide , halide , bromide , medicinal chemistry , lithium (medication) , chloroform , chloride , selectivity , bromine , organic chemistry , catalysis , medicine , endocrinology
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.