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May

Picture of the Month - May 2022

1,2-Carboboration of allenes: A new way to synthesize 1,4-dienes

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The direct carboboration of a double or triple bond, simultaneously forming a new C−C and C−B bond, is an attractive method for the synthesis of organboranes, important intermediates for pharmaceuticals. However, direct carboboration reactions are usually limited to specific Lewis acidic boranes.  We reported now found a more general way for synthesizing Lewis acidic alkenylboranes, which readily undergo carboboration reactions (https://doi.org/10.1002/chem.202200470). These boranes transfer under mild conditions the alkenyl group in a regioselective 1,2-carboboration to arylallenes. The products of this reaction are well suited for the palladium-catalyzed synthesis of aryl-substituted 1,4-dienes. The picture shows crystals of one of the 1,4-dienes and the molecular structure that was derived from single-crystal X-ray diffraction.

This picture was submitted by Dr. Urs Gellrich.


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