期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 20, 页码 7428-7434出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406424
关键词
alkynes; cross-coupling; metal-free; Pummerer; sulfoxide
资金
- EPSRC (Established Career Fellowship)
- Merck Sharp and Dohme
- Novartis
- Leverhulme Trust
- University of Manchester
- M.E.C. Spain
- Universidad de Burgos (Predoctoral Fellowship and Mobility Grant)
- Engineering and Physical Sciences Research Council [EP/M005062/1] Funding Source: researchfish
- EPSRC [EP/M005062/1] Funding Source: UKRI
A sulfoxide-directed, metal-free ortho-propargylation of aromatics and heteroaromatics exploits intermolecular delivery of a propargyl nucleophile to sulfur followed by an intramolecular relay to carbon. The operationally simple cross-coupling procedure is general, regiospecific with regard to the propargyl nucleophile, and shows complete selectivity for products of ortho-propargylation over allenylation. The use of secondary propargyl silanes allows metal-free ortho-coupling to form carbon-carbon bonds between aromatic and heteroaromatic rings and secondary propargylic centres. The 'safety-catch' nature of the sulfoxide directing group is illustrated in a selective, iterative double cross-coupling process. The products of propargylation are versatile intermediates and they have been readily converted into substituted benzothiophenes.
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