Directed Markovnikov hydroarylation and hydroalkenylation of alkenes under nickel catalysis
We report a full account of our research on nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of non-conjugated alkenes, which has yielded a toolkit of methods that proceed under mild conditions with alkenyl sulfonamide, ketone, and amide substrates. Regioselectivity is con...
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Published in | Chemical science (Cambridge) Vol. 12; no. 33; pp. 1138 - 1144 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
CAMBRIDGE
Royal Soc Chemistry
25.08.2021
Royal Society of Chemistry The Royal Society of Chemistry |
Subjects | |
Online Access | Get full text |
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Summary: | We report a full account of our research on nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of non-conjugated alkenes, which has yielded a toolkit of methods that proceed under mild conditions with alkenyl sulfonamide, ketone, and amide substrates. Regioselectivity is controlled through catalyst coordination to the native Lewis basic functional groups contained within these substrates. To maximize product yield, reaction conditions were fine-tuned for each substrate class, reflecting the different coordination properties of the directing functionality. Detailed kinetic and computational studies shed light on the mechanism of this family of transformations, pointing to transmetalation as the turnover-limiting step.
Native Lewis basic functional groups enable the nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of unactivated alkenes with organoboron reagents. |
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Bibliography: | 10.1039/d1sc03121j Electronic supplementary information (ESI) available. See DOI ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 2041-6520 2041-6539 |
DOI: | 10.1039/d1sc03121j |