Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 22, Pages 4213-4220Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610779
Keywords
radical redox relay; titanium catalysis; cobalt catalysis; bimetallic; aziridines; allylic amines; allylic amides
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Funding
- National Institute of General Medical Sciences [R01GM134088]
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A bimetallic radical redox-relay strategy is utilized to generate alkyl radicals with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to achieve base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction offers an alternative approach for the synthesis of allylic amides from alkenes through a three-step sequence, accomplishing a formal transpositional allylic amination.
Herein a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence to accomplish a formal transpositional allylic amination.
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