32110-50-2Relevant articles and documents
Selective benzylic and allylic alkylation of protic nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds
Liu, Cong-Rong,Li, Man-Bo,Yang, Cui-Feng,Tian, Shi-Kai
experimental part, p. 793 - 797 (2009/09/29)
The acid-catalyzed benzylic and allylic alkylation of protic nucleophiles is fundamentally important for the formation of carbon-carbon and carbon-heteroatom bonds, and it is a formidable challenge for benzylic and allylic amine derivatives to be used as the alkylating agents. Herein we report a highly efficient benzylic and allylic alkylation of protic carbon and sulfur nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds at room temperature. In the presence of a catalytic amount of inexpensive ZnCl2-TMSCl (TMSCl: chlorotrimethylsilane), 1,3-diketones, β-keto esters, β-keto amides, malononitrile, aromatic compounds, thiols, and thioacetic acid can couple with a broad range of tosylactivated benzylic and allylic amines to give diversely functionalized products in good to excellent yields and with high regioselectivity. Furthermore, the cross-coupling reaction of 1,3-dicarbonyl compounds with benzylic propargylic amine derivatives has been successfully applied to the one-step synthesis of polysubstituted furans and benzofurans.
Synthesis of (p-Nitroaryl)diarylmethanes via vicarious nucleophilic substitution of hydrogen
Makosza,Surowiec,Voskresensky
, p. 1237 - 1240 (2007/10/03)
(p-Nitroaryl)diarylmethanes are readily prepared via vicariousm nucleophilic substitution of hydrogen in nitroarenes with carbanions of diarylmethyl p-chlorophenyl sulfide. These carbanions are efficient reagents for introduction of diarylmethyl substituents in the para position of nitroarenes via the VNS reaction. The reaction does not proceed ortho to the nitro group due to steric hindrances on the addition step.
