35030-49-0Relevant articles and documents
On the mechanism of conversion of 4-carboxy-3,4-dihydro-3-phenyl-1(2H)-isoquinolones to indeno[1,2-c]isoquinolines by thionyl chloride
Xiao, Xiangshu,Morrell, Andrew,Fanwick, Phillip E.,Cushman, Mark
, p. 9705 - 9712 (2006)
It has been known for a long time that thionyl chloride can effectively mediate the transformation of 4-carboxy-3,4-dihydro-3-phenyl-1(2H)-isoquinolones to indeno[1,2-c]isoquinolines. The mechanism of this unique transformation, however, remains to be established. Evidence is presented to demonstrate that (1) the two-electron dehydrogenation precedes Friedel-Crafts cyclization and (2) the two-electron dehydrogenation occurs via H-4 deprotonation and subsequent O-sulfinylation of the lactam moiety instead of C-sulfinylation of the carbon α to the carboxyl group.
Transition-metal-free and base promoted C-C bond formationviaC-N bond cleavage of organoammonium salts
Chen, Tieqiao,Huang, Tianzeng,Ke, Yuting,Li, Chunya,Liu, Long,Tang, Yuanyuan,Tang, Zhi,Wang, Kunyu,Zhang, Tao
supporting information, p. 8237 - 8240 (2021/10/12)
A transition-metal-free and base promoted C-C bond forming reaction of benzyl C(sp3)-H bond with organoammonium saltsviaC-N bond cleavage has been reported. Benzyl ammonium salts as well as cinnamyl ammonium salt could couple readily with various benzyl C(sp3)-H species, producing the corresponding products in moderate to excellent yields with good functional group tolerance. Late stage chemical manipulation enabled the specific 1,2-diarylethane structure of products transformed into useful olefin compoundsviadehydrogenation, which further demonstrated the utility of this reaction.
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