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Directed Nickel-Catalyzed 1,2-Dialkylation of Alkenes

preprint
revised on 24.01.2018, 00:23 and posted on 24.01.2018, 04:18 by Joseph Derosa, Vincent A. van der Puyl, Van T. Tran, Mingyu Liu, Keary Engle
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.

Funding

1R35GM125052, NSF/DGE-1346837, NSF/DBI-1359160

History

Topic

  • Organic Synthesis and Reactions

Email Address of Submitting Author

keary@scripps.edu

Email Address(es) for Other Author(s)

jderosa@scripps.edu, vavander@scripps.edu, tranvan@scripps.edu, mingyu@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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