Journal
CHEMICAL SCIENCE
Volume 9, Issue 6, Pages 1604-1609Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc04861k
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Funding
- Purdue University
- National Institutes of Health [R35GM124791]
- NSF [CHE-1625543]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1625543] Funding Source: National Science Foundation
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A [i-PrPDI]CoBr2 complex (PDI-pyridine-diimine) catalyzes Simmons-Smith-type reductive cyclopropanation reactions using CH2Br2 in combination with Zn. In contrast to its non-catalytic variant, the cobalt-catalyzed cyclopropanation is capable of discriminating between alkenes of similar electronic properties based on their substitution patterns: monosubstituted > 1,1-disubstituted > (Z)-1,2disubstituted > (E)-1,2-disubstituted > trisubstituted. This property enables synthetically useful yields to be achieved for the monocyclopropanation of polyalkene substrates, including terpene derivatives and conjugated 1,3-dienes. Mechanistic studies implicate a carbenoid species containing both Co and Zn as the catalytically relevant methylene transfer agent.
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