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Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds.

ABSTRACT: A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments.

SUBMITTER: Derosa J

PROVIDER: S-EPMC6001383 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds.

Derosa Joseph J van der Puyl Vincent A VA Tran Van T VT Liu Mingyu M Engle Keary M KM

Chemical science 20180516 23

A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce different ...[more]

PMID: 29997883

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