Xurong Qin

Synthesis of di(hetero)aryl sulfides by directly using arylsulfonyl chlorides as a sulfur source

A new, efficient protocol for the synthesis of di(hetero)aryl sulfides is described. Cheap and easily available arylsulfonyl chlorides as a sulfur source reductively couple with electron-rich (hetero)arenes (e.g., indolizines, indoles, electron-rich benzenes, etc.) in the presence of triphenylphosphine to afford di(hetero)aryl thioethers in good yields.

A Palladium/Copper Bimetallic Catalytic System: Dramatic Improvement for Suzuki–Miyaura‐Type Direct CH Arylation of Azoles with Arylboronic Acids

As a variety of metal-mediated biaryl formations througharomatic C H activation have been popularized, theSuzuki–Miyaura-type reactions, in which aryl halides orpseudohalides are replaced by (hetero)arenes, have recentlyattracted attention. This type of cross-coupling is not onlyan efficient and complementary process to form biaryls, butalso is in connection with sustainable chemistry. Whereasthe Suzuki–Miyaura-type direct C H arylation of arenes(which generally require a directing group) has been devel-oped greatly,

Chelation-assisted Rh(III)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes

The chelation-assisted strategy has been endowed with some novel functions in the Rh(III)-catalyzed dehydrogenative coupling of indoles/pyrroles with heteroarenes. While the reaction conditions used are rather common, the strategy can close the homo-coupling pathway of each coupling partner, and dramatically extend substrate scope along with the exclusive indole or pyrrole C2-site selectivity. This is the first example describing that a catalytic system allows the oxidative C–H/C–H hetero-coupling not only between two electron-rich heteroarenes but also between electron-deficient and electron-rich heteroarenes, showing a further beneficial aspect of the Rh(III) catalysis.

Rh(III)-Catalyzed Decarboxylative ortho-Heteroarylation of Aromatic Carboxylic Acids by Using the Carboxylic Acid as a Traceless Directing Group

Highly selective decarboxylative ortho-heteroarylation of aromatic carboxylic acids with various heteroarenes has been developed through Rh(III)-catalyzed two-fold C-H activation, which exhibits a wide substrate scope of both aromatic carboxylic acids and heteroarenes. The use of naturally occurring carboxylic acid as the directing group avoids troublesome extra steps for installation and removal of an external directing group.

Regiospecific N‐Heteroarylation of Amidines for Full‐Color‐Tunable Boron Difluoride Dyes with Mechanochromic Luminescence

Colors to dye for: Palladium-catalyzed regiospecific N-heteroarylations of amidines with 2-halo-N-heteroarenes leads to a structurally diverse library of BF2 /amidine-based complexes. These dyes not only present full-visible-color solid-state emissions with large Stokes shifts and high fluorescence quantum yields, but also exhibit a full-color-tunable mechanofluorochromic nature.

Copper(II)-catalyzed dehydrogenative cross-coupling between two azoles.

The copper(II)-catalyzed dehydrogenative coupling between two different azoles for the preparation of unsymmetrical biazoles has been developed. The current catalytic system can effectively control the chemoselectivity for heterocoupling over homocoupling.

Palladium(II)‐Catalyzed Oxidative CH/CH Cross‐Coupling between Two Structurally Similar Azoles

Power of two: A widely functional-group tolerant, selective and rapid oxidative cross-coupling between two structurally similar azoles has been carried out by using a palladium/copper co-catalytic twofold C-H activation method (see scheme).

One-pot synthesis of benzofused heteroaryl azoles via tandem C-heteroatom coupling/C–H activation of azoles

The Cu(I) or Pd(II)-catalyzed cross-couplings of gem-dihaloolefins with azoles via tandem C-heteroatom coupling/C-H activation for the preparation of benzofused heteroaryl azoles have been developed.