Electron Transfer Driven Addition of Ketimine Derived Radicals to Arene-Cr(CO)3 Complexes

Oliver Hoffmann; Hans-Günther Schmalz

doi:10.1055/s-1998-1949

Synlett 1998; 1998(12): 1426-1428
DOI: 10.1055/s-1998-1949

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Electron Transfer Driven Addition of Ketimine Derived Radicals to Arene-Cr(CO)₃ Complexes

Oliver Hoffmann^* , Hans-Günther Schmalz

^*Institut für Organische Chemie, Sekr. C3, Technische Universität Berlin, Straße des 17. Juni 135, D-10623 Berlin, Germany; Fax + 30 314-2 11 05; E-mail: schmalz@wap0109.chem.tu-berlin.de

Abstract

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The first examples of SmI₂ mediated radical cyclizations of ketimines have been achieved with η ⁶-arene-Cr(CO)₃ complexes bearing ketimine sidechains. The cyclization products were obtained in high yield and with significant diastereoselectivity. The reactions seem to proceed via addition of azaketyl-type radicals to the complexed arenes to form 17 VE intermediates which are trapped by single electron transfer to give the corresponding (anionic) 18 VE species.

chromium complexes - radical cyclization - samarium(II)iodide - electron transfer - ketimines

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