The Mizoroki‐Heck Reaction with Internal Olefins: Reactivities and Stereoselectivities

The Mizoroki‐Heck reaction is one of the most valuable reactions for functionalizing C−C double bonds in the presence of a Pd catalyst. This protocol is suitable for the reaction of a C(sp2)‐halide with a terminal olefin to produce a trans‐1,2‐disubstituted olefin. However, reports of the Mizoroki‐H...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2020-04, Vol.9 (4), p.480-491
Main Authors: Nakashima, Yusei, Hirata, Goki, Sheppard, Tom D., Nishikata, Takashi
Format: Article
Language:English
Subjects:
Alkenes
Aromatic compounds
C−C bond formation
Halides
internal olefins
Mizoroki-Heck reaction
Organic chemistry
polysubstituted olefins
Reactivity
Stereoselectivity
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Summary:The Mizoroki‐Heck reaction is one of the most valuable reactions for functionalizing C−C double bonds in the presence of a Pd catalyst. This protocol is suitable for the reaction of a C(sp2)‐halide with a terminal olefin to produce a trans‐1,2‐disubstituted olefin. However, reports of the Mizoroki‐Heck reaction of internal olefins are rare and impractical due to the low reactivity of internal olefins and problems of product diastereoselectivity. In this review, we summarize Mizoroki‐Heck reactions of internal olefins with aryl or alkyl halides to illustrate their reactivities and stereoselectivities. Internal olefins are problematic: The Mizoroki Heck is one of the most useful reactions to prepare substituted olefins. However, the reactions of internal olefins are problematic because of low reactivities of internal olefins and poor stereoselectivities. In this review, we briefly introduce this type of chemistry.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900741