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Sulfonyl Acetylenes as Alkynylating Reagents Under Radical or Anionic Conditions
Author(s) -
García Ruano José Luis,
Alemán José,
Parra Alejandro,
Marzo Leyre
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301483
Subject(s) - chemistry , reagent , radical , sulfonyl , alkynylation , moiety , heteroatom , conjugated system , combinatorial chemistry , organic chemistry , alkyl , medicinal chemistry , catalysis , polymer
We provide a summary of the literature describing the use of β‐substituted sulfonylacetylenes as efficient alkynylation reagents in their reactions with radical or anionic species. Such alkynylation is due to the unexpected behavior of ethynyl sulfones, which undergo “ anti ‐Michael” addition of radicals and organolithium reagents and subsequent elimination of the sulfinate moiety. The reaction behavior of alkyl radicals, generated by different procedures, allows the alkynylation of any kind of C(sp 3 ), C(sp 2 ), and C(sp) carbon atoms, being especially efficient for α‐positions to heteroatoms With organolithium reagents alkynylation can be achieved with very few restrictions, providing substituted acetylenes or conjugated enynes of any kind in high yields under very mild conditions. Ynol ethers and alkynylphosphonates are also accessible through reactions with metal alkoxides and trialkyl phosphites, respectively.