131379-16-3Relevant articles and documents
Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: Catalytic enantioselective synthesis of secondary sulfonamides and sulfones
Choi, Junwon,Martín-Gago, Pablo,Fu, Gregory C.
, p. 12161 - 12165 (2014)
The development of efficient methods for the generation of enantioenriched sulfonamides and sulfones is an important objective for fields such as organic synthesis and medicinal chemistry; however, there have been relatively few reports of direct catalytic asymmetric approaches to controlling the stereochemistry of the sulfur-bearing carbon of such targets. In this report, we describe nickel-catalyzed stereoconvergent Negishi arylations and alkenylations of racemic α-bromosulfonamides and -sulfones that furnish the desired cross-coupling product in very good ee and yield for an array of reaction partners. Mechanistic studies are consistent with the generation of a radical intermediate that has a sufficient lifetime to diffuse out of the solvent cage and to cyclize onto a pendant olefin.
Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling
Cao, Qun,Howard, Joseph L.,Wheatley, Emilie,Browne, Duncan L.
supporting information, p. 11339 - 11343 (2018/08/28)
A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.
Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides
Krasovskiy, Arkady,Malakhov, Vladimir,Gavryushin, Andrei,Knochel, Paul
, p. 6040 - 6044 (2007/10/03)
(Chemical Equation Presented) Insider dealing: A wide range of poly-functional (hetero)aromatic and aliphatic zinc reagents can be easily prepared in THF. The compounds are formed by a Zn insertion reaction mediated by the addition of LiCl (see scheme; All = allyl).
