Nucleophilic additions of phenylsulfonyl-substituted tricarbonyl(1,3-cyclohexadiene)iron complexes

Add time:08/01/2019    Source:sciencedirect.com

Tricarbonyl[η4-2-(phenylsulfonyl)-1,3-cyclohexadiene]iron(0) (3) was prepared in good yield from 2-(phenylsulfonyl)-1,3-cyclohexadiene and Fe2(CO)9 using azadiene 2 as the catalyst. The reaction of 3 with nucleophiles proceeded only at the C-4 position under thermodynamic (25°C) or kinetic (−78°C) condition. Careful treatment of 3 with Ph3CPF6 at low temperature regiospecifically gave the tricarbonyl[(1-5-η5)-3-(phenylsulfonyl)cyclohexadienyl]iron(I) complex 6. The η5-complex 6 was more reactive than the η4-complex 3, and reacted with various nucleophiles stereo- and regiospecifically at the C-1 position. The addition products 9 could be demetallated to give functionalized dienyl sulfones 10.

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