35938-56-8Relevant academic research and scientific papers
Use of the 2-Pyridinesulfonyloxy Leaving Group for the Fast Copper-Catalyzed Coupling Reaction at Secondary Alkyl Carbons with Grignard Reagents
Shinohara, Riku,Morita, Masao,Ogawa, Narihito,Kobayashi, Yuichi
supporting information, p. 3247 - 3251 (2019/05/10)
Investigation of the copper-catalyzed coupling reaction of 2-pyridinesulfonates with Grignard reagents revealed that reactions with catalytic Cu(OTf)2 were completed in 40 min. The results differed from those of the previous CuI-catalyzed reactions of tosylates in the presence of additives (LiOMe and TMEDA) for 12-24 h. It was shown that the preferred coordination of the leaving group to the reagents accelerated the reaction. Successful reagents were MeMgCl and other RMgX. Complete inversion was established.
Nickel-catalyzed alkyl-alkyl cross-coupling reactions of non-activated secondary alkyl bromides with aldehydes as alkyl carbanion equivalents
Zhu, Chenghao,Zhang, Junliang
supporting information, p. 2793 - 2796 (2019/03/06)
A novel nickel-catalyzed alkyl-alkyl cross coupling of non-activated secondary alkyl bromides with aldehydes via hydrazone intermediates has been developed. Aldehydes as alkyl carbanion equivalents replace traditional organometallic reagents. This coupling occurs on the carbon of the hydrazone rather than the nitrogen. In addition, non-activated primary and tertiary alkyl bromides also undergo the cross-coupling reaction to form new C(sp3)-C(sp3) bonds in moderate yields.
Sulfoxide-modified Julia-Lythgoe olefination: Highly stereoselective di-, tri-, and tetrasubstituted double bond formation
Pospisil, Jiri,Pospisil, Tomas,Marko, Istvan E.
, p. 1953 - 1969 (2007/10/03)
A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SmI 2/HMPA or SmI2/DMPU-mediated reductive elimination, 1,2-di-, tri- and tetrasubstituted olefins in moderate to good yields and E/Z selectivity. The conditions are mild and the procedure is widely applicable. The reaction mechanism was studied and a general model, describing the reaction selectivity, is proposed.
Sulfoxides in Julia-Lythgoe olefination: Efficient and stereoselective preparation of di-, tri-, and tetrasubstituted olefins
Pospisil, Jiri,Pospisil, Tomas,Marko, Istvan E.
, p. 2373 - 2376 (2007/10/03)
(Chemical Equation Presented) A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and Sml2/HMPA- or DMPU-mediated reductive elimination, 1,2-di-, tri-, and tetrasubstituted olefins in moderate to excellent yields and E/Z selectivity. The conditions are mild, and the procedure is broadly applicable.
THREO SELECTIVE CROSS ALDOL CONDENSATION WITH THIOAMIDE ENOLATES GENERATED BY A MICHAEL ADDITION OF ORGANOMETALLICS TO UNSATURATED THIOAMIDES
Tamaru, Y.,Hioki, T.,Yoshida, Z.
, p. 5793 - 5796 (2007/10/02)
Crotonthioamide, sorbothioamide, and cinnamothioamide undergo a threo selective aldol condensation via their enolates generated by a Michael addition of organometallics.
