Aqueous/Nonaqueous DBU Mixtures: Versatile Switching Media for Chemoselective Aldol, Baylis‐Hillman, and Aldol Condensation Reactions

ChemistryOpen, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

Abstract Isophorone is a relatively small molecule with several neighboring reacting sites, making it susceptible to various competing reactions aldehydes, including aldol, Baylis‐Hillman (BH), aldol condensation, and Michael addition reactions. In the present work, we have designed switchable 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU)‐catalyzed procedure, where reaction of isophorone aldehydes guided chemoselectively toward either BH, or condensation reactions, depending on use water and/or heat. This controllable divergency likely stems from ability tune dual nucleophilicity/basicity characters DBU/H 2 O medium. other words, nucleophilicity DBU plays crucial role in directing process formation BH adducts absence water. At same time, pathway dominates when present. The conditions were amenable for tandem processes, as demonstrated an condensation/Diels‐Alder sequence.

Язык: Английский

Facile synthesis of β‐trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation of a‐trifluoromethyl styrenes with thiols

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(20)

Опубликована: Июль 23, 2024

Abstract A very simple and atom‐economical method for the synthesis of vicinal trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation α‐(trifluoromethyl)styrenes with thiols was reported. The reaction proceeded smoothly under mild conditions provided β‐CF 3 ‐thioethers in moderate to good yields an anti‐Markovnikov manner. Furthermore, this features several remarkable advantages, such as use a catalytic amount DBN, broad substrate scope, excellent functional group compatibility, easy scalability.

Язык: Английский

Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4H-benzo[4,5]imidazo[2,1-b][1,3]thiazine

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 26, 2024

A base-controlled synthesis of N -β-CF 3 -substituted 2 H -benzo[ d ]imidazole-2-thiones and 2-fluoro-4 -benzo[4,5]imidazo[2,1- b ][1,3]thiazines via hydroamination or defluorinative cyclizations α-CF -styrenes with 2-mercaptobenzimidazole was developed.

Язык: Английский