Journal
ACS CATALYSIS
Volume 11, Issue 6, Pages 3473-3477Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c00404
Keywords
radicals; dual catalysis; photocatalysis; amination; imidate radicals
Categories
Funding
- National Institutes of Health [R35 GM119812]
- National Science Foundation [CAREER 1654656]
- Sloan Research Foundation
- Eli Lilly
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A dual catalytic strategy involving an Ir photocatalyst and a Cu complex enables regioselective amination and cross-coupling of allyl alcohols with various nucleophiles. This approach allows for the formation of N-radicals via an energy transfer mechanism followed by interception of alkyl radicals for radical amino-functionalizations of olefins. Insights into the nature of Cu-based radical interception are provided through stereo, regio, and kinetic probes.
The regioselective amination and cross-coupling of a range of nucleophiles with allyl alcohols has been enabled by a dual catalytic strategy. This approach entails the combined action of an Ir photocatalyst that enables mild access to N-radicals via an energy transfer mechanism, as well as a Cu complex that intercepts the ensuing alkyl radical upon cyclization. Merger of this Cucatalyzed cross-coupling enables a broad range of nucleophiles (e.g., CN, SCN, N-3, vinyl, allyl) to engage in radical amino-functionalizations of olefins. Notably, stereo, regio, and kinetic probes provide insights into the nature of this Cu-based radical interception.
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