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

Nakashima, Y; Hirata, G; Sheppard, TD; Nishikata, T; (2020) The Mizoroki-Heck Reaction with Internal Olefins: Reactivities and Stereoselectivities. Asian Journal of Organic Chemistry , 9 (4) pp. 480-491. 10.1002/ajoc.201900741. Green open access

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Abstract

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(sp^{2})-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.

Type: Article
Title: The Mizoroki-Heck Reaction with Internal Olefins: Reactivities and Stereoselectivities
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/ajoc.201900741
Publisher version: https://doi.org/10.1002/ajoc.201900741
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Mizoroki-Heck reaction, internal olefins, C−C bond formation, stereoselectivity, polysubstituted olefins
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10091916
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