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Ligandless Iron-Catalyzed Desulfinylative C–C Allylation Reactions using Grignard Reagents and Alk-2-enesulfonyl Chlorides

Authors

  • Chandra M. R. Volla,

    1. Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Federal Institute of Technology-Lausanne (EPFL), Batochime, 1015, Lausanne, Switzerland, Fax: +41-21-693-9375
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  • Dean Marković,

    1. Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Federal Institute of Technology-Lausanne (EPFL), Batochime, 1015, Lausanne, Switzerland, Fax: +41-21-693-9375
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  • Srinivas Reddy Dubbaka,

    1. Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Federal Institute of Technology-Lausanne (EPFL), Batochime, 1015, Lausanne, Switzerland, Fax: +41-21-693-9375
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  • Pierre Vogel

    1. Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Federal Institute of Technology-Lausanne (EPFL), Batochime, 1015, Lausanne, Switzerland, Fax: +41-21-693-9375
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Abstract

Alk-2-enesulfonyl chlorides 14 were synthesized by the BCl3-promoted ene reaction of alkenes with SO2. These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard reagents (aromatic, aliphatic, andheteroaromatic). The reaction can be catalyzed with even 2 mol-% of the simple iron salt Fe(acac)3. The regioselectivity of these allylations was studied by using sulfonyl chlorides 3 and 4 with aryl Grignard reagents. The scope of these allylations was further extended by the coupling of ester-substituted alk-2-enesulfonyl chloride 10 with aromatic Grignard reagents. Symmetrical products were synthesized by double C–C allylation with the use of 2-methylidenepropane-1,3-disulfonyl chloride (12). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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