A highly efficient method for the
selective formal C–H/C–H
cross-coupling of azoles and (hetero)arenes was established through
arylsulfonium intermediates under transition-metal catalysis, which
produced a variety of 2-(hetero)aryl azoles in good to excellent yields.
Advantages of the reaction included mildness, a good functional group
tolerance, a wide range of substrates, a high regio- and chemoselectivity,
one-pot procedures, and the late-stage functionalization of complex
molecules without the use of oxidants, offering a promising strategy
for the transition-metal-catalyzed C–H arylation of azoles.
Deuteration of arylthianthren-5-ium triflates with CD 3 OD or CD 3 OD/CD 3 COCD 3 in the presence of Cs 2 CO 3 by palladium catalysis or photoirradiation allowed the convenient synthesis of deuterated arenes in good yields. The Pd-catalyzed reaction generally gave better yields than the photoinduced deuteration, but exceptions also exist. They could complement each other in some cases. These reactions featured eco-friendly conditions, simplicity, inexpensive deuterium sources, good functional group tolerance, and a range of substrates. Since arylthianthren-5-ium salts could be readily synthesized from arenes and thianthrene 5-oxide, this protocol provided a formal aromatic C−H deuteration with high selectivity, enabling efficient deuterium labeling of multifunctionalized arenes and drug molecules.
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