Journal
NATURE CATALYSIS
Volume 2, Issue 3, Pages 211-218Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/s41929-018-0219-x
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Funding
- UK Engineering and Physical Sciences Research Council [EP/M005062/01]
- UK Engineering and Physical Sciences Research Council (Established Career Fellowship)
- Engineering and Physical Sciences Research Council UK National EPR Facility and Service at the University of Manchester [NS/A000055/1]
- EPSRC [EP/P001386/1, EP/R029938/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/P001386/1, EP/R029938/1] Funding Source: researchfish
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Radical cyclization cascades are powerful tools used to construct the complex three-dimensional structures of some of society's most prized molecules. Since its first use 40 years ago, SmI2 has been used extensively for reductive radical cyclizations. Unfortunately, SmI2 must almost always be used in significant excess, thus raising issues of cost and waste. Here, we have developed radical cyclization cascades that are catalysed by SmI2 and exploit a radical relay/electron-catalysis strategy. The approach negates the need for a super-stoichiometric co-reductant and requires no additives. Complex cyclic products, including products of dearomatization, containing up to four contiguous stereocentres are obtained in excellent yield. Mechanistic studies support a single-electron-transfer radical mechanism. Our strategy provides a long-awaited solution to the problem of how to avoid the need for stoichiometric amounts of SmI2 and establishes a conceptual platform on which other catalytic radical processes using the ubiquitous reducing agent can be built.
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