Sulfoxide-Directed Metal-Free ortho-Propargylation of Aromatics and Heteroaromatics.

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 readi

SUBMITTER: Eberhart AJ 

PROVIDER: S-EPMC4524421 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature