A rapid synthesis of 1-chloro-2-arylcyclohexenes using MWAOS in aqueous media: single crystal studies of two representative compounds

Abstract

A novel methodology for the rapid synthesis of 11 1-chloro-2-arylcyclohexenes in 89–95% yields, employing the regioselective Suzuki-Miyaura cross-coupling reaction, under microwave conditions in aqueous media is reported. The products formed in less than 7 minutes duration. The crystal structures of two representative compounds of 1-chloro-2-arylcyclohexenes, with biphenyl- and naphthyl- substituents have been analyzed. The compounds crystallized in the monoclinic system with P2₁/n and P2₁ space groups, respectively, and are stabilized by two weak interactions C-H···Cl and C-H···Cg.

Keywords:

• Aqueous reactions
• halogenated arylcyclohexenes
• MWAOS
• regioselective Suzuki-Miyaura cross-coupling
• single crystal XRD

Acknowledgments

The authors thank (i) Bangalore University, Bangalore; (ii) Bengaluru Central University, Bengaluru; and (iii) JCAS for a Council of Scientific and Industrial Research (CSIR), Govt. of India, New Delhi, INDIA; CSIR SRF – File no. 09/039(0119)/2018-EMR-1, dated April 16, 2018 to JCAS.