Generation and Reactions of o-Bromophenyllithium without Benzyne Formation Using a Microreactor

Generation and Reactions of o-Bromophenyllithium without Benzyne Formation Using a Microreactor

Microflow systems were found to serve as powerful tools for mechanistic studies on reactions involving highly unstable intermediates such as o-bromophenyllithium, which is known to decompose to benzyne very quickly even at −78 °C. Precise residence time control and precise temperature control of mic...

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Veröffentlicht in:Journal of the American Chemical Society 2007-03, Vol.129 (11), p.3046-3047
Hauptverfasser: Usutani, Hirotsugu, Tomida, Yutaka, Nagaki, Aiichiro, Okamoto, Hideho, Nokami, Toshiki, Yoshida, Jun-ichi
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container_end_page 3047
container_issue 11
container_start_page 3046
container_title Journal of the American Chemical Society
container_volume 129
creator Usutani, Hirotsugu
Tomida, Yutaka
Nagaki, Aiichiro
Okamoto, Hideho
Nokami, Toshiki
Yoshida, Jun-ichi
description Microflow systems were found to serve as powerful tools for mechanistic studies on reactions involving highly unstable intermediates such as o-bromophenyllithium, which is known to decompose to benzyne very quickly even at −78 °C. Precise residence time control and precise temperature control of microsystems are responsible. Based on the information thus obtained, the Br−Li exchange reaction of o-dibromobenzene followed by reactions with electrophiles without benzyne formation was achieved using a microflow system. Sequential use of two bromine atoms in o-dibromobenzene with Br−Li exchange reactions followed by the reactions with electrophiles using the microsystem consisting of four micromixers and four microtube reactors was also accomplished.
doi_str_mv 10.1021/ja068330s
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title Generation and Reactions of o-Bromophenyllithium without Benzyne Formation Using a Microreactor
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