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

Eberhart AJ, Shrives HJ, Álvarez E, Carrër A, Zhang Y, Procter DJ - Chemistry (2015)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (UK), Fax: (+44) 161-275-4939 http://people.man.ac.uk/∼mbdssdp2/

No MeSH data available.


A safety-catch directing group for metal-free propargylation. DG=directing group.
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sch02: A safety-catch directing group for metal-free propargylation. DG=directing group.


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

Eberhart AJ, Shrives HJ, Álvarez E, Carrër A, Zhang Y, Procter DJ - Chemistry (2015)

A safety-catch directing group for metal-free propargylation. DG=directing group.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4524421&req=5

sch02: A safety-catch directing group for metal-free propargylation. DG=directing group.
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (UK), Fax: (+44) 161-275-4939 http://people.man.ac.uk/∼mbdssdp2/

No MeSH data available.