Weak bonding strategies for achieving regio- and site-selective transformations

Yang Jiao, Xiao Yang Chen*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

13 Scopus citations

Abstract

The ability to identify and transform selectively similar constitutional fragments in molecules in a predetermined direction over all other possible directions remains a fundamental challenge in relation to the growth and reach of synthetic chemistry. A rapidly emerging approach toward this goal is to leverage weak bonding interactions, including both noncovalent and dynamic covalent bonds to control regio- and site selectivities. Drawing inspiration from the reactions catalyzed by enzymes, chemists have developed a wide variety of weak bonding strategies to facilitate regio- and site-selective transformations without the need to introduce additional handles onto molecular frameworks. Here, by classifying these weak bonding protocols into four categories, namely, bond-destabilizing, masking, pre-organizing, and templating strategies, we summarize the advances that have been made during the past two decades, highlighting their relative simplicity in promoting regio- and site-selective reactions that would otherwise be difficult to perform on molecules.

Original languageEnglish (US)
Pages (from-to)414-438
Number of pages25
JournalChem
Volume8
Issue number2
DOIs
StatePublished - Feb 10 2022

Keywords

  • SDG12: Responsible consumption and production
  • SDG3: Good health and well-being
  • dynamic covalent bonds
  • host-guest chemistry
  • nanoconfinement
  • noncovalent bonding interactions
  • pre-organization
  • regioselectivity
  • supramolecular catalysis

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry

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