Palladium/Norbornene Cocatalyzed Catellani‐Type Domino Reaction with Aryl Diazonium Salts

Abstract

The palladium/norbornene co‐catalyzed difunctionalization of haloarenes provides a facile and efficient method for the synthesis of polyfunctional aromatic compounds. However, the suitable substrates for such a transformation have been strictly limited to haloarenes. We here demonstrate that aryl diazonium salts could be well employed as substrates in these reactions, enabling arylbromides with electron‐withdrawing groups to be used as cross‐coupling partners.

Catalytic ortho C–H methylation and trideuteromethylation of arylthianthrenium salts via the Catellani strategy

“…11 In recent decades, Lautens, 12 Dong, 13 Zhou, 14 Liang, 15 and other researchers 16 have made significant advancements in this field, establishing this methodology as a reliable route for synthesizing complex arenes. In contrast to the diverse variations of nucleophilic and electrophilic reagents, the substrates used in Catellani-type reactions have been mainly confined to aryl halides (triflates), 11,17,18 aryl thioesters, 19 aryl diazonium salts, 20 aryl boronic acids, 21 vinyl halides (triflates), 22,23 indoles, 24 carbazoles, 25 thiophenes, 26 and arenes with directing groups, 27 and the exploitation of arylthianthrenium salts has remained elusive (Scheme 1d). 28 In this paper, we report the ortho C–H methylation and trideuteromethylation of arylthianthrenium salts enabled by the Catellani reaction (Scheme 1e).…”

Catalytic Ortho C-H Methylation and Trideuteromethylation of Ar-ylthianthrenium Salts via the Catellani Strategy

“…In recent decades, Lautens, 12 Dong, 13 Zhou, 14 Liang, 15 and other researchers 16 have made significant advancements in this field, establishing this methodology as a reliable route for synthesizing complex arenes. In contrast to the diverse variations of nucleophilic and electrophilic reagents, the substrates used in Catellani-type reactions have been mainly confined to aryl halides (triflates), 11,17,18 aryl thioesters, 19 aryl diazonium salts, 20 aryl boronic acids, 21 vinyl halides (triflates), 22,23 indoles, 24 carbazoles, 25 arenes with directing groups, 26 and the exploitation of arylthianthrenium salts has remained elusive (Scheme 1d). In this paper, we reported the first ortho C−H methylation and trideuteromethylation of arylthianthrenium salts enabled by Catellani reaction (Scheme 1e).…”

Nickel-Catalyzed Cross-Coupling of Aryl Diazonium Salts with Aryl Bromides

“…Aryl diazonium salts can be readily synthesized from aromatic amines and have proven be superior reagents in recent years, due to their ability to be transformed into a wide range of significant organic molecules and synthetic blocks through various organic reactions . The Heck–Matsuda and Suzuki reactions of aryl diazonium salts, catalyzed by palladium, represent excellent cross-coupling reactions and may function as electrophilic reagents in C–H arylation processes . In this case, scientists have formulated coupling reactions involving electrophilic diazonium salts and various nucleophilic reagents under the metal catalysis, such as arylmagnesium, arylzinc, and aryl boronic acid, among others (Scheme a) .…”