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Ligandless Iron-catalyzed Desulfinylative C-C Allylation reactions using Grignard reagents and Alk-2-enesulfonyl Chlorides

Alk-2-enesulfonyl chlorides 1–4 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).

Desulfinylative C-C allylation reactions; Grignard reagents; Alk-2-enesulfonyl Chlorides

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