Reactivity trends for mechanochemical reductive coupling of aryl iodides. Issue 1 (2nd January 2023)

• Record Type: Journal Article
• Authors: Carson, Courtney; Hassing, Joshua; Olguin, Trinity; Peterson, Karl P.; Haley, Rebecca A.
• Is Part Of: Green chemistry letters and reviews. Volume 16:Issue 1(2023)
• Publication Date: 2023-01-02
• Subjects: Green chemistry -- dimethyl carbonate -- mechanochemistry -- N-butyl pyrrolidinone; Green chemistry -- Periodicals; 540
• DOI: 10.1080/17518253.2022.2153628
• Languages: English
• ISSNs: 1751-8253

Abstract

ABSTRACT: Reductive coupling reactions are a facile and versatile way to make carbon – carbon bonds. However, most methods within this class of reactions makes use of reprotoxic, amide-based solvents. Mechanochemistry, a method that does not always require solvent, has been used for reductive coupling methods but still reports the use of at least some amide-based solvent for productive outcomes. This work presents the reactivity trends for the reductive homocoupling of aryl iodides when using various amounts of N, N -dimethylformamide (a commonly used amide-based solvent) and dimethyl carbonate (a greener alternative). The results of these experiments show that dimethyl carbonate may be used in sub-stoichiometric amounts with equal or greater efficiency to N, N -dimethyl formamide. Further, cross-electrophile coupling (XEC) is explored with various solvents, showing that N -butyl pyrrolidinone is efficient as a liquid assisted grinding solvent. These experiments show that under mechanochemical conditions, safer solvents are able to be used with no loss of efficacy for reductive coupling reactions. GRAPHICAL ABSTRACT: UF0001