4.8 Article

Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 42, Pages 13103-13106

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705521

Keywords

allylation; electrophiles; nickel; quaternary carbon centers; tertiary alkyl halides

Funding

  1. Chinese NSF [21372151, 21572127]
  2. Shanghai Peak Discipline Construction [13-A302-15-L02]

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The construction of all C(sp(3)) quaternary centers has been successfully achieved under Ni-catalyzed cross-electrophile coupling of allylic carbonates with unactivated tertiary alkyl halides. For allylic carbonates bearing C1 or C3 substituents, the reaction affords excellent regioselectivity through the addition of alkyl groups to the unsubstituted allylic carbon terminus. The allylic alkylation method also exhibits excellent functional-group compatibility, and delivers the products with high Eselectivity.

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