Electrochemically enabled rhodium-catalyzed [4 + 2] annulations of arenes with alkynes

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 23; no. 23; pp. 9515 - 9522
• Main Authors: Wang, Zi-Chen, Li, Rui-Tao, Ma, Qiang, Chen, Jia-Yi, Ni, Shao-Fei, Li, Ming, Wen, Li-Rong, Zhang, Lin-Bao
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 29.11.2021; Royal Society of Chemistry
• Subjects: air; Alkynes; Aqueous solutions; Aromatic compounds; aromatic hydrocarbons; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; electricity; electrochemistry; Electrolysis; Functional groups; Green & Sustainable Science & Technology; Green chemistry; Oxidants; Oxidizing agents; Physical Sciences; regioselectivity; Rhodium; Science & Technology; Science & Technology - Other Topics; stoichiometry; Substrates; FUNCTIONALIZATION; ALKENES; ACTIVATION; ORIGINS; C-H BOND; ACIDS; OXYGENATION; STRATEGY; MECHANISMS; ALKENYLATION
• ISSN: 1463-9262; 1463-9270; 1463-9270
• DOI: 10.1039/d1gc03187b

Herein, electrochemically driven, Rh( iii )-catalyzed regioselective annulations of arenes with alkynes have been established. The strategy, combining the use of a rhodium catalyst with electricity, not only avoids the need for using a stoichiometric amount of external oxidant, but also ensures that the transformations proceed under mild and green conditions, which enable broad functional group compatibility with a variety of substrates, including drugs and pharmaceutical motifs. Moreover, the electrolysis reaction was made operationally simple by employing an undivided cell, and proceeds efficiently in aqueous solution in air. Herein, electrochemically driven, Rh( iii )-catalyzed regioselective annulations of arenes with alkynes have been established.