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Synlett 1998; 1998(5): 549-551
DOI: 10.1055/s-1998-1695
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Reductive Pinacol Coupling of Aromatic Carbonyl Compounds Catalytic in Chromium(II)

Aleš Svatoš* , Wilhelm Boland
  • *Max-Planck Institute for Chemical Ecology, Tatzendpromenade 1a, D-07745 Jena, Germany; Fax + 49(0)36 41-64 36 63; E-mail: Boland@ice.mpg.de
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Publication History

Publication Date:
31 December 2000 (online)

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Reductive coupling of aromatic and heteroaromatic aldehydes and ketones bearing different functional groups to pinacols is effectively catalysed with 1-5 mol% of Cr(II) salts or chromocene in THF/DMF mixtures in the presence of manganese powder and trialkyl chlorosilanes. Excellent dl selectivity can be achieved albeit with lower yield using trialkylsilyl chlorides with bulky substituents.

single-electron reduction - additive - silyloxy radical - stereocontrol - chromium(II) catalysis - pinacol coupling