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Iridium‐Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis
Author(s) -
Yu Peng,
Bismuto Alessandro,
Morandi Bill
Publication year - 2020
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.201912803
Subject(s) - halide , iridium , catalysis , chemistry , silylation , reagent , organic chemistry , hydrogen halide , functional group , combinatorial chemistry , halogen , alkyl , polymer
Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium‐catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4‐chlorobutan‐2‐one or tert ‐butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional‐group tolerance and safety profile of these reactions compared to the state‐of‐the‐art. This method has granted access to alkenyl halide compounds containing acid‐sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram‐scale synthesis where low catalyst loading was achieved.