Sulfoxide-Directed Metal-Free ortho-Propargylation of Aromatics and Heteroaromatics.
Chemistry
; 21(20): 7428-34, 2015 May 11.
Article
em En
| MEDLINE
| ID: mdl-25752800
ABSTRACT
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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MEDLINE
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En
Ano de publicação:
2015
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Article