Boshun Wan

A regio- and chemoselective molecular-bridging strategy for natural terpenyl aldehydes and terpenes with Ts-hydrazine has been developed through pyrazole formation.

Under the irradiation of visible light, an efficient catalyst-free strategy for imino functionalizations of alkenes has been developed via the formation of an EDA complex.

In this article, we disclose a method for the regiodivergent and stereoselective hydrosilylation of isoprene using an Earth-abundant cobalt catalyst via variation of ligands. With a less sterically hindered bidentate ligand, the reactions proceeded through 4,1-hydrosilylation to afford allylsilanes in excellent regio- and stereoselectivities. By switching to a bulkier ligand, the reactions were efficiently diverted to 2,1-addition products for the first time. This regiodivergent protocol provides a modular approach for the construction of structurally diverse organosilanes with high atom economy and without the formation of stoichiometric byproducts.

The recent surge in the applications of deuterated drug candidates has rendered an urgent need for diverse deuterium labeling techniques. Herein, an efficient Rh-catalyzed deuterated Tsuji-Wilkinson decarbonylation of naturally available aldehydes with D₂O is developed. In this reaction, D₂O not only acts as a deuterated reagent and solvent but also promotes Rh-catalyzed decarbonylation. In addition, decarbonylative strategies for the synthesis of terminal monodeuterated alkenes from α,β-unsaturated aldehydes are within reach.

Diaryl 1,3,5‐triazines are not only important linkers in various covalent‐ and metal‐organic frameworks but also versatile electron acceptors in host materials for organic light‐emitting diodes (OLEDs). We herein report C−H acetoxylation, benzoxylation, methoxylation, and halogenation of a diverse array of diaryl 1,3,5‐triazines under palladium catalysis. Both symmetrical and nonsymmetrical diaryltriazines are viable substrates. This work offers a potential alternative to the existing methods in preparation or modification of functional materials.

This review comprehensively summarizes the advances achieved in catalytic intermolecular annulations of ynamides from 2010 to 2020.

A distinct copper-catalyzed boroacylation of allenes with acyl chlorides and bis(pinacolato)diboron is developed. For aromatic acyl chlorides, 1,2-boroacylation of allenes readily takes place, leading to the formation of tetrasubstituted vinylboronates with exclusive (E)-stereoselectivity. In comparison, the employment of alkyl acyl chlorides as electrophiles alters the selectivity to 2,3-boroacylated products. Additionally, the product can easily undergo Suzuki–Miyaura cross-coupling to afford tetrasubstituted alkene with complete retention of the configuration.

Through the oxidative addition of cobalt into the N–C(O) bond of phthalimide and the subsequent decarbonylation, we describe an efficient cobalt-catalyzed intermolecular decarbonylative carboamidation of alkynes. High regioselectivities have been achieved for unsymmetrical alkynes (including aryl–alkyl or aryl–aryl) to deliver polysubstituted isoquinolones. To facilitate step economy, a three-component decarbonylative carboamidation of alkynes with phthalic anhydrides and amines has been demonstrated using the current cobalt catalysis.

With chiral 2-methoxy-1-naphthylsulfinyl-based phenyl backbone sulfoxide-olefin ligands, a highly Rh-catalyzed addition of aryl­boronic acids to N,N-dimethylsulfamoyl-protected aldimines has been developed to afford a broad range of chiral diarylmethylamines in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Moreover, efficient enantioselective arylation of cyclic N-sulfonylimines was also achieved with excellent enantioselectivities (up to 98% ee).

A ruthenium-catalyzed allylic C(sp ³ )–H activation strategy has been employed to develop an intermolecular coupling of alkenyl sulfonamides with alkynes.