170803-79-9Relevant academic research and scientific papers
A Titanium-Catalyzed Reductive α-Desulfonylation
Kern, Christoph,Selau, Jan,Streuff, Jan
supporting information, p. 6178 - 6182 (2021/03/16)
A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst-dependent mechanism involving a homolytic C?S cleavage.
Sulfone–Metal Exchange and Alkylation of Sulfonylnitriles
Yang, Xun,Nath, Dinesh,Gau, Michael R.,Steward, Omar W.,Fleming, Fraser F.
supporting information, p. 7257 - 7260 (2017/06/13)
The first general sulfone–metal exchange is described. Treating substituted 2-pyridylsulfonylacetonitriles with either BuLi or Bu3MgLi generates metalated nitriles that efficiently intercept a variety of electrophiles to afford quaternary nitriles. The 2-pyridylsulfone is critical for the sulfone–metal exchange because chelation anchors the organometallic proximal to the electrophilic, tetrasubstituted sulfone to override complex-induced deprotonation. Alkylating commercial 2-pyridinesulfonylacetonitrile with mild bases, either K2CO3 or DBU, and subsequent sulfone–metal exchange and alkylation rapidly assembles quaternary nitriles by three alkylations, only one of which requires an organometallic reagent.
Two-Carbon Elongation/Annulation of Alcohols to Nitriles
Lai, Jing-Yu,Yu, Jurong,Hawkins, R. David,Falck, J. R.
, p. 5691 - 5694 (2007/10/02)
Alcohols were replaced by a two-carbon nitrile unit in good to excellent yields via dehydrative alkylation with (phenylsulfonyl)acetonitrile under modified Mitsunobu conditions followed by desulfonylation using magnesium.Diols and haloalcohols furnished cycloalkylnitriles.
SYNTHESIS OF THE NITRILES AND AMIDES OF 1-(ARYLSULFONYL)CYCLOALKANESCARBOXYLIC ACIDS
Neplyuev, V. M.,Bazavova, I. M.,Esipenko, A. N.,Lozinskii, M. O.
, p. 1712 - 1716 (2007/10/02)
1-Arylsulfonylcycloalkanecarbonitriles were synthesized by the cycloalkylation of arylsulfonylacetonitriles by terminal dihalogenoalkanes under the conditions of phase-transfeer catalysis.Hydrolysis of the products gave 11-arylsulfonylcycloalkanecarboxyli
