Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene–palladium complex catalyst

• Guangming Nan,
• Fang Ren and
• Meiming Luo

Beilstein J. Org. Chem. 2010, 6, No. 70, doi:10.3762/bjoc.6.70

• a solution of NaNO2 (10 mmol) in cold water (1 mL) was added dropwise. The resulting solution of the diazonium salt was stirred in the cold for 10 min and then added all at once to a chilled solution of pyrrolidine (11 mmol) in 1 M KOH (10 mL). The reaction mixture was stirred for 30 min with

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• -trifluoromethylation of phenol by diazonium salt 19a. Effect of the counteranion. Thermal O- and N-trifluoromethylations. Method of preparation of S-(trifluoromethyl)diphenylsulfonium triflates. Reactivity of some S-(trifluoromethyl)diarylsulfonium triflates. One-pot synthesis of S-(trifluoromethyl)diarylsulfonium

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

• Mohan Mahesh,
• John A. Murphy,
• Franck LeStrat and
• Hans Peter Wessel

Beilstein J. Org. Chem. 2009, 5, No. 1, doi:10.3762/bjoc.5.1

• vinblastine (58a) and vincristine (58b) contain such a system. Aryl C-C bond formation As a final extension of this methodology, we probed the feasibility of this methodology in aryl-aryl C-C bond formation reactions. Accordingly, the diazonium salt 62 was prepared from indoline (59), and treated with one

• could also undergo direct formation of the radical 69. Rearomatization from 69 might then occur through a number of pathways; in one of these, the radical intermediate 69 would lose a proton to yield the radical anion 70 which, upon oxidation by loss of single electron to the starting diazonium salt 62