Electrochemical Synthesis of Hetero[7]helicenes Containing Pyrrole and Furan Rings <i>via</i> an Oxidative Heterocoupling and Dehydrative Cyclization Sequence-Reference-Cited by-同舟云学术

Electrochemical Synthesis of Hetero[7]helicenes Containing Pyrrole and Furan Rings via an Oxidative Heterocoupling and Dehydrative Cyclization Sequence

Published:2023-01-24 Issue:3 Volume:365 Page:373-380
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Salem Mohamed S. H.¹²^ORCID,Khalid Md. Imrul¹,Sako Makoto³,Higashida Keigo¹,Lacroix Charlie⁴,Kondo Masaru⁵,Takishima Ryo⁶,Taniguchi Taisei⁶,Miura Masahiro⁷^ORCID,Vo‐Thanh Giang⁴,Sasai Hiroaki¹³^ORCID,Takizawa Shinobu¹^ORCID

Affiliation:

1. SANKEN Osaka University Ibaraki-shi Osaka 567-0047 Japan

2. Pharmaceutical Organic Chemistry Department Faculty of Pharmacy Suez Canal University Ismailia 41522 Egypt

3. Graduate School of Pharmaceutical Sciences Osaka University Suita-shi Osaka 565-0871 Japan

4. Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), CNRS-UMR 8182 Laboratoire de Catalyse Moléculaire Université Paris-Saclay 91405 Orsay Cedex France

5. Department of Materials Science and Engineering Graduate School of Science and Engineering Ibaraki University Hitachi-shi Ibaraki 316-8511 Japan

6. Department of Applied Chemistry Graduate School of Engineering Osaka University Suita-shi Osaka 565-0871 Japan

7. Innovative Catalysis Science Division Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI) Osaka University Suita-shi Osaka 565-0871 Japan

Abstract

AbstractThe electrochemical synthesis of hetero[7]helicenes including pyrrole and furan rings has been established. A single electrochemical operation led to an oxidative heterocoupling and dehydrative cyclization sequence to afford oxaza[7]helicenes in 50–86% yields with 45–77% Faradic efficiencies. Their derivatization and chiroptical properties were also investigated.

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Funder

Ministry of Education, Culture, Sports, Science and Technology

Hoansha Foundation

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202201262

Reference102 articles.

1. Recent reviews and reports on the synthesis of helicenes see: