Arylsulfonylacetylenes as Alkynylating Reagents
The unexpected “anti-Michael” addition of RLi to β-substituted sulfonylacetylenes, followed by in situ elimination of the ion sulfinate, allows the alkynylation of C(sp2) and C(sp3). Aryl and heteroaryl acetylenes, enynes, and mono and dialkyl
alkynes can be obtained in very high yields under very mild conditions, avoiding the use of transition metals as catalysts and, in many cases, haloderivatives as starting materials. Furthermore, the use of lithium 2-p-tolylsulfinyl benzylcarbanions as nucleophiles of these reactions
allows their stereocontrolled alkynylation, affording enantiomerically pure alkynes or enantioenriched allenes depending on the protonating agent (NH4Cl or H2O).
Keywords: Alkynylation; C(sp2)-C(sp) and C(sp3)-C(sp) bonds; organolithiums; sulfonylacetylenes; “anti-Michael” reactions
Document Type: Research Article
Affiliations: Departamento de Química Orgánica (Módulo 1), Universidad Autónoma de Madrid, Cantoblanco, Madrid, Spain
Publication date: 01 April 2013
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