One‐Step Construction of 9,10‐Diarylphenanthrenes Using Solid Calcium Carbide as an Alternative of Gaseous Acetylene

• Published in: Asian journal of organic chemistry 2024-10, Vol.13 (10), p.n/a
• Main Authors: Liu, Zhenrong, Wang, Zhiqiang, Li, Zheng
• Format: Article
• Language: English
• Subjects: 9,10-Diarylphenanthrenes; Acetylene; Alkyne source; Alkynes; Calcium carbide; Calcium compounds; Carbides; Cascade reaction; Chemical bonds; C−H activation; Explosive bonding; One-pot multi-component reaction; Substrates
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.202400235

A convenient method for the construction of 9,10‐diarylphenanthrenes through one‐pot multicomponent reactions of iodoarenes, o‐bromobenzoic acids, and calcium carbide is described. A series of target compounds are efficiently synthesized via Csp2−H activation and the simultaneous construction of five C−C bonds. The salient features of this method are the use of inexpensive and easy‐to‐handle solid alkyne source as an alternative of flammable and explosive gaseous acetylene. Meanwhile the use of commercially available substrates, wide functional tolerance, and simple workup procedure are also advantage of this protocol. In addition, the corresponding products can also be synthesized on gram scale. This work describes a strategy for the one‐step construction of 9,10‐diarylphenanthrenes using inexpensive, abundant and easy‐to‐handle solid calcium carbide instead of flammable and explosive gaseous acetylene as an alkyne source, commercially available iodoarenes and o‐bromobenzoic acids as starting materials. The target compounds with potential applications in functional materials and pharmaceuticals are effectively obtained via the simultaneous construction of five carbon–carbon bonds.