5217-04-9Relevant academic research and scientific papers
Formation of quaternary carbons through cobalt-catalyzed C(sp3)-C(sp3) Negishi cross-coupling
Palao, Eduardo,López, Enol,Torres-Moya, Iván,De La Hoz, Antonio,Díaz-Ortiz, ángel,Alcázar, Jesús
, p. 8210 - 8213 (2020/08/17)
Formation of all-carbon-substituted quaternary carbons is a key challenge in organic and medicinal chemistry. We report a cobalt-catalyzed C(sp3)-C(sp3) cross-coupling that allows for the introduction of benzyl, heteroarylmethylzinc and allyl groups to halo-carbonyl substrates. The cross-coupling reaction is selective for C(sp3)-over C(sp2)-halides, in contrast to most used catalytic metals, and allows access to novel scaffolds of pharmaceutical interest. NMR mechanistic studies suggest the presence of Co(0) complexes as catalytic species. This journal is
Copper-catalyzed intramolecular C(sp3)-H and C(sp2)-H amidation by oxidative cyclization
Wang, Zhen,Ni, Jizhi,Kuninobu, Yoichiro,Kanai, Motomu
supporting information, p. 3496 - 3499 (2014/04/03)
The first copper-catalyzed intramolecular C(sp3)-H and C(sp 2)-H oxidative amidation has been developed. Using a Cu(OAc) 2 catalyst and an Ag2CO3 oxidant in dichloroethane solvent, C(sp3)-H
Nickel-catalyzed site-selective amidation of unactivated C(sp 3)-H bonds
Wu, Xuesong,Zhao, Yan,Ge, Haibo
supporting information, p. 9530 - 9533 (2014/08/18)
Intramolecular dehydrogenative cyclization of aliphatic amides was achieved on unactivated sp3 carbon atoms by a nickel-catalyzed C-H bond functionalization process with the assistance of a bidentate directing group. The reaction favors the C-H bonds of β-methyl groups over the γ-methyl or β-methylene groups. Additionally, a predominant preference for the β-methyl C-H bonds over the aromatic sp2 C-H bonds was observed. Moreover, this process also allows for the effective functionalization of benzylic secondary sp3 C-H bonds. β-Lactams from nickel catalysis: Intramolecular dehydrogenative cyclization of aliphatic amides was achieved on unactivated sp3 carbon atoms by a nickel-catalyzed C-H bond functionalization process with the assistance of a bidentate directing group (see scheme).
Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers
Nishimoto, Yoshihiro,Saito, Takahiro,Yasuda, Makoto,Baba, Akio
experimental part, p. 5462 - 5471 (2009/12/01)
The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.
Utilization of Bu3SnSiMe3 in organic synthesis II. New cyclization by a stannyl anion generated from Bu3SnSiMe3 and R4NX
Mori, Miwako,Kaneta, Naotake,Shibasaki, Masakatsu
, p. 35 - 40 (2007/10/02)
A new cyclization reaction of an aryl or vinyl halide bearing a carbonyl group such as ketone or ester has been developed by use of a stannyl anion generated in DMF from Bu3SnSiMe3 and Bu4NCl.Key words: Trimethylsilyl; Stannyl anion
