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In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor
Author(s) -
Kandasamy Mohanraj,
Huang Yu Hsuan,
Ganesan Balaji,
Senadi Gopal Chandru,
Lin WeiYu
Publication year - 2019
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.201900471
Subject(s) - negishi coupling , chemistry , flow chemistry , reagent , acetylide , aryl , coupling reaction , halide , in situ , zinc , reaction conditions , combinatorial chemistry , organic chemistry , photochemistry , catalysis , alkyl
A highly efficient and convenient Negishi cross‐coupling reaction has been developed for the synthesis of unsymmetrical alkynes and enynes in a continuous‐flow process. The reaction proceeds through an in situ generated alkynylzinc reagent by the reaction of lithium acetylide with zinc halide at room temperature followed by a cross‐coupling reaction with aryl or vinyl iodides. The notable features of this work compared to the conventional benchtop method are mild reaction conditions, good to excellent yields, broad functional‐group compatibility, short residence time (73 sec) and especially desilylation of TMS group with the residence time of only 10.5 sec.