313058-73-0Relevant academic research and scientific papers
Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings
Plunkett, Shane,Basch, Corey H.,Santana, Samantha O.,Watson, Mary P.
supporting information, p. 2257 - 2262 (2019/03/04)
A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the noncanonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance.
Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides
Liao, Jennie,Basch, Corey H.,Hoerrner, Megan E.,Talley, Michael R.,Boscoe, Brian P.,Tucker, Joseph W.,Garnsey, Michelle R.,Watson, Mary P.
supporting information, p. 2941 - 2946 (2019/04/30)
A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.
Synthesis of Cp*CH2PPh2 and its use as a ligand for the nickel-catalysed cross-coupling reaction of alkyl halides with aryl Grignard reagents
Uemura, Minoru,Yorimitsu, Hideki,Oshima, Koichiro
, p. 4726 - 4728 (2007/10/03)
A new ligand, Cp*CH2PPh2 (Cp* = 1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl), was prepared, and was used as a ligand for nickel-catalysed cross-coupling reaction of alkyl halides with aryl Grignard reagents, which nickel-phosphine complexes had never made possible. The Royal Society of Chemistry.
Integrated chemical process: One-pot aromatization of cyclic enones by the double elimination methodology
Orita, Akihiro,Yaruva, Jayamma,Otera, Junzo
, p. 2267 - 2270 (2007/10/03)
A variety of aromatic hydrocarbons bearing multiple alkyl substituents are accessible with perfect regiocontrol in a one-pot reaction starting from cyclo-hexenones and their aromatic analogues [Eq. (1)]. The present methodology can be further extended to the synthesis of polycyclic aromatic hydrocarbons. The drawbacks encountered in the Friedel-Crafts reaction are resolved since the reaction proceeds under basic conditions.
