Abstract
The consecutive addition of acyl radicals and N-alkylindole nucleophiles to styrenes was established, as well as some additional radical–nucleophile combinations. Both aryl and aliphatic aldehydes give reasonable yields. The reaction proceeds best for α-substituted styrenes, effectively creating a quaternary all-carbon center. Some iridium-based photoredox systems are catalytically active; furthermore, a base is needed in this transformation. Radicals are formed by reductive perester cleavage and hydrogen atom transfer.
Highlights
Alkylindole nucleophiles to styrenes was established, as well as some additional radical−nucleophile combinations
The consecutive addition of a radical and a nucleophile to the C C bond of an olefin is an interesting method of olefin difunctionalization, as it allows the introduction of two complementary reagents in a single step.[1]
We present a photoredox method of olefin difunctionalization by addition of radicals formed by Hydrogen Atom Transfer (HAT) together with nucleophiles to styrenes, generating products of type 4, especially β-indolyl ketones (Scheme 1)
Summary
Letter quenching mode is operating (for experimental details and extended mechanistic discussions, see the Supporting Information). To date, it has been very common for methods of radical difunctionalizations of olefins to have strong limitations. Apart from our work shown here (see 6f above), there is only one procedure that could successfully apply a p-cyano-substituted styrene.3d Most methods are limited to electron-rich styrenes, which is not the case for difunctionalizations with other nucleophiles. Support from the DFG (KL 2221/7-1 and Heisenberg scholarship to M.K., KL 2221/4-2) and from the MPI für Kohlenforschung is gratefully acknowledged. The authors thank Jörg Rust and Conny Wirtz (both MPI für Kohlenforschung) for X-ray crystal analysis and NMR measurements, respectively
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