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Continuous‐Flow Synthesis of Biaryls Enabled by Multistep Solid‐Handling in a Lithiation/Borylation/Suzuki–Miyaura Cross‐Coupling Sequence
Author(s) -
Shu Wei,
Pellegatti Laurent,
Oberli Matthias A.,
Buchwald Stephen L.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105223
Subject(s) - borylation , modular design , sequence (biology) , modularity (biology) , computer science , coupling (piping) , aryl , combinatorial chemistry , flow (mathematics) , scheme (mathematics) , database , chemistry , organic chemistry , programming language , mathematics , materials science , biochemistry , alkyl , geometry , biology , metallurgy , genetics , mathematical analysis
Let it flow : An efficient and modular synthesis of biaryls under continuous‐flow conditions has been realized by a lithiation/borylation/Suzuki–Miyaura cross‐coupling sequence under ambient conditions. Aryl bromides and heteroaromatic precursors can be transformed in the room‐temperature lithiation reaction with n BuLi, followed by borylation and Suzuki–Miyaura coupling with the aid of ultrasonic irradiation (see scheme).