Jin-Tao Yu

The carbomethylation of arylacrylamides leading to 3-ethyl-3-substituted indolin-2-one by cascade radical addition/cyclization

An FeCl2-promoted carbomethylation of arylacrylamides by di-tert-butyl peroxide (DTBP) is achieved, leading to 3-ethyl-3-substituted indolin-2-one in high yield. The reaction tolerates a series of functional groups, such as cyano, nitro, ethyloxy carbonyl, bromo, chloro, and trifluoromethyl groups. The radical methylation and arylation of the alkenyl group are involved in this reaction.

Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal.

The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.

The Bu4NI-catalyzed alfa-acyloxylation of ketones with benzylic alcohols.

The Bu4NI-catalyzed reaction of ketones with benzylic alcohols was achieved, leading to alfa-acyloxycarbonyl compounds in moderate to good yields. This metal-free procedure featured the employment of facilely and commercially available starting materials and TBHP as a clean oxidant with high atom economy.

Palladium-Catalyzed Cyanation of Aryl Halides with CuSCN

A palladium-catalyzed cyanation of aryl halides and borons has been developed by employing cuprous thiocyanate as a safe cyanide source. This protocol avoids the use of a highly toxic cyanide source, providing aromatic nitriles in moderate to good yields with good functional tolerance.

Di-tert-butyl peroxide-promoted α-alkylation of α-amino carbonyl compounds by simple alkanes.

A di-tert butyl peroxide (DTBP)-promoted α-alkylation of α-amino carbonyl compounds by simple alkanes is developed, proceeding through dual sp(3) C-H bonds cleavage. The reaction was applicable for α-amino ketones and α-amino esters, providing a facile pathway for the α-functionalization of these substrates. The radical pathway is involved in this transformation.

Metal-Free Radical Oxidative Annulation of Ynones with Alkanes To Access Indenones

The benzoyl peroxide (BPO) promoted carboannulation of ynones with alkanes is developed, affording a series of 2-alkyl-3-aryl indenones in moderate to good yields. The procedure involves direct functionalization of alkane C(sp(3))-H and arene C(sp(2))-H bonds under metal-free conditions, providing a favorable approach for indenone synthesis.

Copper-Catalyzed N-Cyanation of Sulfoximines by AIBN

The direct copper-catalyzed N-cyanation of sulfoximines was achieved by using AIBN as a safe cyanide source. It represents a simple and environmentally benign procedure for the construction of the N-CN bond. Furthermore, some sec-amines can also be tolerated well under this procedure.

A copper-mediated oxidative N-cyanation reaction

Copper-promoted N-cyanation of aliphatic sec-amine by CuCN is achieved via oxidative coupling. This procedure employs O2 as a clean oxidant. Notably, sulfoximines and 1,1,3,3-tetramethylguanidine also worked well in this procedure. Thus, it represents a key progress in the C-N bond formation reaction as well as in the cyanation reaction.

tert-Butyl peroxybenzoate-promoted α-methylation of 1,3-dicarbonyl compounds.

A tert-butyl peroxybenzoate (TBPB)-promoted direct α-methylation of 1,3-dicarbonyl compounds has been developed, providing α-methyl derivatives in moderate to good yields. In this procedure, TBPB plays a dual role, serving as both the methyl source and radical initiator. This work represents a key complement to the traditional α-methylation of 1,3-dicarbonyl compounds using methyl iodide.

Copper-catalyzed N-thioetherification of sulfoximines using disulfides

A novel copper-catalyzed N-thioetherification of sulfoximines under mild reaction conditions was developed. In this procedure, the N-S bond formation was achieved using readily available disulfides as the sulfur source.