Synthesis of new silylated sulfur-containing heterocycles through thionation of bis(acylsilanes)
Reaction of bis(acylsilanes), with spacers of variable size, with HMDST affords symmetrical and unsymmetrical silylated thiophene-, thiopyran- and dihydrothiepine derivatives.
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Acknowledgements
The authors gratefully acknowledge Professor Alfredo Ricci, University of Bologna, for helpful discussions.
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Towards bis(acylsilanes) and cyclic unsaturated acylsilanes via metathesis: an exploratory study
2009, TetrahedronCitation Excerpt :These conditions were applied for all allyl- and vinyl(acyl)silanes prepared through dithiane intermediates 3 (Table 1). Similarly, after numerous attempts to hydrolyze the benzotriazole-substituted intermediates 4, we decided to investigate ferric chloride (method B), a Lewis acid, which catalyzes effectively ketal hydrolysis.10 The conversion of intermediates 4 into the corresponding acylsilanes 1 was eventually achieved using anhydrous ferric chloride in acetone (Table 1).
Chapter 5.1 Five-membered ring systems: thiophenes and Se/Te analogues
2005, Progress in Heterocyclic ChemistryCitation Excerpt :An interesting application of thiophene-2-boronic acid 66 provided a route to fused benzo[b]thiophenes 67 [X = O, NTs, C(CO2Me)2] upon treatment with yne-propargylic carbonates 68 in the presence of [Pd(PPh3)4] <04CEJ5338>. An iterative strategy for the synthesis of oligothiophene derivatives based on Suzuki or Stille coupling reactions has been described <04HC121>, while Stille reactions have also been used for the preparation of donor–acceptor substituted oligothiophenes <04T4071>, or radial oligothienyl silanes <04TL3109>. Poorly soluble quinque- and sexithiophenes have been prepared by solution-phase microwave assisted chemistry based on Suzuki couplings <04JOC4821>.
Chapter 6.4 Six-membered ring systems: with O and/or S atoms
2005, Progress in Heterocyclic ChemistryCitation Excerpt :The anionic polycondensation of acetonaphthones 56 with homophthalates gives dibenzo[b,j] xanthones and offers an approach to the naturally occurring hypoxyxylerone system <04SL2693> . 2,6-Disilylated 4H-thiopyrans are formed by the thionation of 1,5-bis(acylsilanes) presumably via the thioacylsilane (Scheme 22) <04TL87> . The heptynoate sulfoxides 57 obtained in three steps from 3,3-dimethylbut-1-yne are cyclised to tetrahydrothiopyrans on treatment with diethylzinc under Pd-catalysis; the overall process is an intramolecular sulfinylzincation.
Silicon-assisted synthesis and functionalization of sulfurated and selenated compounds
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