JOURNAL ARTICLE
RESEARCH SUPPORT, N.I.H., EXTRAMURAL
RESEARCH SUPPORT, NON-U.S. GOV'T
RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
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Catalysis of Radical Cyclizations from Alkyl Iodides under H 2 : Evidence for Electron Transfer from [CpV(CO) 3 H]<sup/>.

Radical cyclizations are most often achieved with Bu3 SnH in the presence of a radical initiator, but environmental considerations demand that alternative reagents be developed-ones that can serve as a synthetic equivalent to the hydrogen atom. We have revisited [CpV(CO)3 H]- , a known replacement for Bu3 SnH, and found that it can be used catalytically under H2 in the presence of a base. We have carried out tin-free catalytic radical cyclizations of alkyl iodide substrates. The reactions are atom-efficient, and the conditions are mild, with broad tolerance for functional groups. We have, for example, achieved the first 5-exo radical cyclization involving attack onto a vinyl chloride. We suggest that the radicals are generated by an initial electron transfer.

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