57918-95-3Relevant articles and documents
Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids
Fan, Zhoulong,Park, Han Seul,Yu, Jin-Quan,Zhu, Ru-Yi
supporting information, p. 12853 - 12859 (2020/06/10)
Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.
Electroreductive Intramolecular Coupling of Nonconjugated Aromatic Ketones
Kise, Naoki,Suzumoto, Takeshi,Shono, Tatsuya
, p. 1407 - 1413 (2007/10/02)
The electroreduction of nonconjugated aromatic ketones gave intramolecularly coupled products.The best result was obtained using an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte.This reductive cyclization proceeded with remarkable stereoselectivity, and the cis isomer was obtained exclusively.A variety of new bi- and polycyclic compounds were synthesized.The reaction mechanism was studied, and it was suggested that the anion radical generated by one-electron transfer to a carbonyl group attacks an aromatic ring intramolecularly.The choice of counter cation of the anion radical was critical for the reductive cyclization.Other reductive methods employing metal reducing agents were also studied.Reduction with Na in HMPA-THF gave the same cyclized product, though the yield was lower than that with the electroreduction.