Benzhydryl phenyl sulfone

In the title compound, C19H16O2S, the sulfur-bound phenyl group is approximately parallel to one of the two phenyl rings of the benzhydryl group, making a dihedral angle of 12.53 (10)°, and forms a dihedral angle of 41.25 (9)° with the other phenyl ring. In the crystal, weak C—H⋯O inter­actions form a two-dimensional network propagating along the bc plane

Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates.

The imidazoles 1a–g add to the CC-double bond of the iminium ion 2 with rate constants as predicted by the equation log k = sN(N + E). Unfavourable proton shifts from the imidazolium unit to the enamine fragment in the adduct 3 account for the failure of imidazoles to take part in iminium-activated aza-Michael additions to enals

4,4′-Bis(dimethylamino)benzhydryl phenyl sulfone

In the title compound, C23H26N2O2S, the sulfur-bound phenyl group is aligned approximately parallel to one of the two rings of the benzhydryl group, making a dihedral angle of 1.15 (9)°. The other forms a dihedral angle of 59.20 (9)° with the phenyl group bound to the S atom. In the crystal, molecules are linked into strands along [100] by weak C—H...O contacts. Weak C–H...π interactions are also observed

Synthesis of Chiral 1,2-Oxazinanes and Isoxazolidines via Nitroso Aldol Reaction of Distal Dialdehydes

The first catalytic enantioselective nitroso aldol reaction of distal dialdehydes is reported. The reaction is catalyzed by simple l-proline at room temperature and subsequent reduction delivered biologically potent and synthetically versatile N–O bond containing five- and six-membered heterocycles, 1,2-oxazinanes, and isoxazolidines in high yields and excellent enantioselectivities (up to >99% ee). The method was further exploited to prepare chiral 3-hydroxypiperidines and -pyrrolidines that are otherwise difficult to access

Nucleopalladation Guided Three-Component Vicinal and Geminal Dicarbofunctionalization of Allylamines

A palladium(II)-catalyzed vicinal as well as geminal selective dicarbofunctionalization of allylamine embedded in a removable picolinamide auxiliary is developed by exploiting nucleopalladation triggered intermolecular three-component coupling reaction. The vicinal selectivity was accomplished by engaging allylamine, indoles, and aryl or styrenyl halides through a Pd(II)/Pd(IV) reaction manifold, while the two-fold coupling of allylamine and indoles via Pd(II)/Pd(0) reaction modality resulted in geminal selectivity. The protocol is operationally simple, scalable, and offers two distinct types of products bearing functionalized tryptamine and bisindolyl frameworks in very high to excellent yields. The reaction features a wide substrate generality and also remains effective in the presence of various medicinally relevant scaffolds. Notably, this work represents the first example of nucleopalladation-guided intermolecular dicarbofunctionalizations of allylamines

Copper-Catalyzed 8‑Aminoquinoline-Directed Selenylation of Arene and Heteroarene C–H Bonds

An efficient copper-catalyzed/-mediated and 8-aminoquinoline-assisted arylselenylation of inert C–H bonds of (hetero)­arenes with readily available diselenides has been reported. The reaction is scalable and tolerates a wide spectrum of functional groups to deliver diarylselenides in very high yields (up to 98%). Application of this methodology to the facile synthesis of thiophene-fused selenochromone was demonstrated

Copper-Catalyzed 8‑Aminoquinoline-Directed Selenylation of Arene and Heteroarene C–H Bonds

An efficient copper-catalyzed/-mediated and 8-aminoquinoline-assisted arylselenylation of inert C–H bonds of (hetero)­arenes with readily available diselenides has been reported. The reaction is scalable and tolerates a wide spectrum of functional groups to deliver diarylselenides in very high yields (up to 98%). Application of this methodology to the facile synthesis of thiophene-fused selenochromone was demonstrated

Copper-Catalyzed 8‑Aminoquinoline-Directed Selenylation of Arene and Heteroarene C–H Bonds

An efficient copper-catalyzed/-mediated and 8-aminoquinoline-assisted arylselenylation of inert C–H bonds of (hetero)­arenes with readily available diselenides has been reported. The reaction is scalable and tolerates a wide spectrum of functional groups to deliver diarylselenides in very high yields (up to 98%). Application of this methodology to the facile synthesis of thiophene-fused selenochromone was demonstrated