Facile synthesis of diiodoheteroindenes and understanding their Sonogashira cross-coupling selectivity for the construction of unsymmetrical enediynes-Reference-Cited by-同舟云学术

Facile synthesis of diiodoheteroindenes and understanding their Sonogashira cross-coupling selectivity for the construction of unsymmetrical enediynes

Published:2024 Issue:20 Volume:22 Page:4096-4107
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Ponomarev Alexander V.¹,Danilkina Natalia A.¹^ORCID,Okuneva Julia S.¹,Vidyakina Aleksandra A.¹^ORCID,Khmelevskaya Ekaterina A.¹^ORCID,Bunev Alexander S.²^ORCID,Rumyantsev Andrey M.³^ORCID,Govdi Anastasia I.¹^ORCID,Suarez Thomas⁴,Alabugin Igor V.⁴^ORCID,Balova Irina A.¹^ORCID

Affiliation:

1. Institute of Chemistry, Saint Petersburg State University (SPbU), Saint Petersburg, 199034, Russia

2. Medicinal Chemistry Center, Tolyatti State University, 445020 Tolyatti, Russia

3. Department of Genetics and Biotechnology, Saint Petersburg State University (SPbU), Saint Petersburg, 199034, Russia

4. Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA

Abstract

Iodocyclization of Ar-iodoacetylenes yields 2,3-diiodoheteroindene substrates for C2-regioselective Sonogashira cross-couplings. The high selectivity observed for diiodobenzothiophene allows the one-pot synthesis of unsymmetrical enediynes.

Funder

Russian Science Foundation

Saint Petersburg State University

National Science Foundation

Publisher

Royal Society of Chemistry (RSC)

Link

http://pubs.rsc.org/en/content/articlepdf/2024/OB/D4OB00530A

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