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Monolithiation of 5,5′‐Dibromo‐2,2′‐bithiophene Using Flow Microreactors: Mechanistic Implications and Synthetic Applications
Author(s) -
Nagaki Aiichiro,
Jiang Yiyuan,
Yamashita Hiroki,
Takabayashi Naoshi,
Takahashi Yusuke,
Yoshida Jun-ichi
Publication year - 2019
Publication title -
chemical engineering and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.403
H-Index - 81
eISSN - 1521-4125
pISSN - 0930-7516
DOI - 10.1002/ceat.201900057
Subject(s) - microreactor , yield (engineering) , residence time (fluid dynamics) , chemistry , flow chemistry , product (mathematics) , medicinal chemistry , catalysis , nuclear chemistry , materials science , organic chemistry , metallurgy , geometry , geotechnical engineering , mathematics , engineering
The lithiation of 5,5′‐dibromo‐2,2′‐bithiophene with one equivalent of an alkyllithium such as n ‐BuLi or s ‐BuLi was studied by varying the residence time in flow microreactors. With a short residence time, the product 2,2′‐bithiophene (3) derived from dilithiation was obtained preferentially and a significant amount of the starting material 5,5′‐dibromo‐2,2′‐bithiophene remained unchanged. An increase in the residence time caused a higher yield of the product 5‐bromo‐2,2′‐bithiophene derived from monolithiation with expense in the yields of 2,2′‐bithiophene and 5,5′‐dibromo‐2,2′‐bithiophene. The lithiation using MeLi gave the product 5‐bromo‐2,2′‐bithiophene preferentially even with a very short residence time.