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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Ru(II)-Catalyzed [4 + 2]-Annulation and Arylation of 1,4-Naphthoquinones
Shreemoyee Kumar1, Akshay M Nair1, Jatin Patra1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Abstract:
Naphthoquinones form the core of a variety of drugs and natural products. As a result, the conjugation of 1,4-naphthoquinones with organic building blocks would offer a facile strategy toward scaffolds of biological interest. In this regard, we hereby report a Ru(II)-catalyzed [4 + 2] annulation of 1,4-naphthoquinones with benzoic acids to afford various naphthoquinone lactones. Additionally, ketone directed arylation of naphthoquinones using acetophenones under Ru(II)-catalysis was also illustrated. The feedstock availability of these precursors allowed access to a large library of naphthoquinone derivatives in good to excellent yields under fairly mild conditions. The practicality of these protocols was justified by carrying out a gram scale synthesis and further functionalizations. Also, preliminary mechanistic studies were carried out to probe the reaction mechanism.
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