The Power of Iodane-Guided C−H Coupling: A Group-Transfer Strategy in Which a Halogen Works for Its Money

Wei W. Chen, Ana B. Cuenca, Alexandr Shafir

Research output: Indexed journal article Reviewpeer-review

31 Citations (Scopus)

Abstract

Hypervalent organoiodane reagents are ubiquitous in organic synthesis, both as oxidants and as electrophilic group-transfer agents. In addition to these hallmark applications, a complementary strategy is gaining momentum that exploits the ability of λ3-iodanes to undergo iodine-to-arene group transfer, for example, via iodonio-Claisen-type rearrangement processes. This Minireview discusses recent advances in the use of this method to access a variety of the C−H-functionalized iodoarenes. While Section 2 is focused on the ortho C−H propargylation, allylation, and the more unusual para C−H benzylation, Section 3 is devoted to the C-arylation of enol and phenol substrates. The accompanying discussion includes mechanistic considerations and goes into the synthetic applications of the final iodoarene cores. The Minireview concludes with further conceptual extensions of the method, including the use of non-conventional coupling partners (for example, cyanoalkylation), improved access to λ3-iodane building blocks, and the development of iterative approaches to polysubstituted iodoarenes.

Original languageEnglish
Pages (from-to)16294-16309
Number of pages16
JournalAngewandte Chemie - International Edition
Volume59
Issue number38
DOIs
Publication statusPublished - 14 Sept 2020

Keywords

  • C−H functionalization
  • haloarenes
  • hypervalent iodine
  • iodane-directed coupling
  • rearrangements

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