Salt Metathesis: An Ultimate Click Reaction

Overview

Journal Precis Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2025 Feb 28

PMID 40018451

Authors

Christopher M Butch

Patrick C Hillesheim

Arsalan Mirjafari

Affiliations

Soon will be listed here.

Abstract

In this Comment, we suggest salt metathesis (or ion exchange) as an ultimate click reaction, extending click chemistry principles beyond covalent bonds to ionic interactions. These universal and robust reactions, which nature utilizes in marine organisms' biomineralization processes, proceed spontaneously under mild conditions with minimal waste, embodying the core principles of click philosophy. This perspective expands the traditional scope of click chemistry and opens new opportunities in synthetic accessibility across organic, inorganic, and materials science spaces.

References

Tornoe C, Christensen C, Meldal M . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem. 2002; 67(9):3057-64. DOI: 10.1021/jo011148j. View

Roy R, Bhagyalalitha M, Choudhury P, Dastidar P . Salt metathesis for developing injectable supramolecular metallohydrogelators as a multi-drug-self-delivery system. Chem Commun (Camb). 2016; 52(95):13811-13814. DOI: 10.1039/c6cc07712a. View

Killops K, Campos L, Hawker C . Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry. J Am Chem Soc. 2008; 130(15):5062-4. DOI: 10.1021/ja8006325. View

Rostovtsev V, Green L, Fokin V, Sharpless K . A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed Engl. 2002; 41(14):2596-9. DOI: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4. View

Sun S, Homer J, Smedley C, Cheng Q, Sharpless K, Moses J . Phosphorus fluoride exchange: Multidimensional catalytic click chemistry from phosphorus connective hubs. Chem. 2024; 9(8):2128-2143. PMC: 11172371. DOI: 10.1016/j.chempr.2023.05.013. View

Dong J, Krasnova L, Finn M, Sharpless K . Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry. Angew Chem Int Ed Engl. 2014; 53(36):9430-48. DOI: 10.1002/anie.201309399. View

Mack J, Tari S, Kaner R . Enhanced solid-state metathesis routes to carbon nanotubes. Inorg Chem. 2006; 45(10):4243-6. DOI: 10.1021/ic060232k. View

Kolb H, Finn M, Sharpless K . Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40(11):2004-2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. View

Castelvecchi D, Ledford H . Chemists who invented revolutionary 'click' reactions win Nobel. Nature. 2022; 610(7931):242-243. DOI: 10.1038/d41586-022-03087-8. View

10.

Kahil K, Weiner S, Addadi L, Gal A . Ion Pathways in Biomineralization: Perspectives on Uptake, Transport, and Deposition of Calcium, Carbonate, and Phosphate. J Am Chem Soc. 2021; 143(50):21100-21112. PMC: 8704196. DOI: 10.1021/jacs.1c09174. View

11.

Lozada J, Lin W, Cao-Shen R, Astoria Tai R, Perrin D . Salt Metathesis: Tetrafluoroborate Anion Rapidly Fluoridates Organoboronic Acids to give Organotrifluoroborates. Angew Chem Int Ed Engl. 2023; 62(16):e202215371. DOI: 10.1002/anie.202215371. View