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Synthesis 2024; 56(24): 3815-3828
DOI: 10.1055/a-2418-8285
DOI: 10.1055/a-2418-8285
short review
Special Topic Dedicated to Prof. Erick Carreira
Merging the Reactivity of (Pseudo)cyclic Hypervalent Iodine Reagents and Carbenes or Carbenoids
We thank École Polytechnique Fédérale de Lausanne (EPFL, Switzerland ) for financial support. This publication was created as part of NCCR catalysis, a National Centre of Competence in Research funded by the Swiss National Science Foundation (Grant No. 180544). Dr. Nieves P. Ramirez thanks the Generalitat Valenciana for a APOSTD 2022 postdoctoral fellowship (CIAPOS/2021/31).
Dedicated to Prof. Erick M. Carreira at the occasion of his 60th birthday
Abstract
In this short review, we present applications merging the reactivity of cyclic hypervalent iodine reagents with carbenes and carbenoids developed in the period 2014–2024. The use of more stable cyclic hypervalent iodine reagents has led to major advances in this area. The combination of iodine(III) chemistry with carbenes or carbenoids enables new disconnections that are not possible using classical reactivity. Both the use of hypervalent iodine compounds as partners in reactions with metal carbenes and as reagents combining the reactivity of iodine(III) and carbenes in a single molecule to give carbyne equivalents are discussed in this review.
1 Introduction
2 Transfer of Fluorinated Groups (F, CF3)
3 Oxy- and Aminoalkyn(en)ylation
3.1 Oxy- and Aminoalkynylation with Acceptor-Substituted Diazo Compounds
3.2 Oxyalkenylation with Acceptor-Substituted Diazo Compounds
3.3 Oxyalkynylation with Acceptor-Acceptor-Substituted Diazo Compounds
4 Carbyne Equivalents
4.1 Diazo-Based Reagents
4.2 Sulfur Ylide Based Reagents
5 Conclusion
Key words
Umpolung - carbenes - carbenoids - cyclic hypervalent iodine reagents - transition-metal catalysis - photocatalysisPublication History
Received: 07 June 2024
Accepted after revision: 19 September 2024
Accepted Manuscript online:
19 September 2024
Article published online:
24 October 2024
© 2024. Thieme. All rights reserved
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Selected examples:
Selected reviews for propargylic amines: