Issue 31, 2023
From the journal:

Organic & Biomolecular Chemistry

ipso-Cyclization of unactivated biaryl ynones leading to thio-functionalized spirocyclic enones†

Chada Raji Reddy, ORCID logo *a   Uprety Ajaykumar,a   Amol D. Patil ORCID logo a  and  Remya Ramesh ORCID logo a  

* Corresponding authors

a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad - 500007, India
E-mail: rajireddy@iict.res.in

Abstract

Ceric ammonium nitrate (CAN)-promoted oxidative ipso-cyclization of unactivated biaryl ynones with S-centered radicals (SCN/SCF3) to access spiro[5,5]trienones has been established. This approach displayed excellent regioselectivity towards spirocyclization and tolerated a variety of functional groups. Dearomatization of hitherto unknown aryl/heteroaryl groups is also disclosed. DMSO is employed as a low-toxicity, inexpensive solvent as well as a source of oxygen.

Graphical abstract: ipso-Cyclization of unactivated biaryl ynones leading to thio-functionalized spirocyclic enones

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Article information

DOI
https://doi.org/10.1039/D3OB00974B
Article type
Paper
Submitted
20 Jun 2023
Accepted
18 Jul 2023
First published
18 Jul 2023

Org. Biomol. Chem., 2023,21, 6379-6388

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ipso-Cyclization of unactivated biaryl ynones leading to thio-functionalized spirocyclic enones

C. R. Reddy, U. Ajaykumar, A. D. Patil and R. Ramesh, Org. Biomol. Chem., 2023, 21, 6379 DOI: 10.1039/D3OB00974B

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