Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 9, Issue 44, Pages 14937-14945Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.1c05307
Keywords
N-C(O) activation; Buchwald-Hartwig amination; green-solvent selection; 2-methyltetrahydrofuran; 2-MeTHF; methyl tert-butyl ether; twisted amides; activated amides
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Funding
- Natural Science Basic Research Program of Shaanxi [2020JQ-238]
- Young Talent Fund of University Association for Science and Technology in Shaanxi [2019-02-02]
- National Natural Science Foundation of China [32001930]
- Innovation Capability Support Plan of Shaanxi Province [2020TD-035]
- Rutgers University
- NSF [CAREER CHE-1650766]
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Solvent selection is crucial in chemical processes, and this study evaluated green solvents for acyl Buchwald-Hartwig cross-coupling, providing the first green-solvent selection guide for this process. Results identified MTBE and 2-MeTHF as preferred alternative solvents with superior properties.
The selection of solvents is essential as a suitable reaction milieu in chemical processes of industrial and academic impact. We present an evaluation of a range of green solvents for acyl Buchwald-Hartwig cross-coupling of amides to provide the first green-solvent selection guide for this powerful C-N to C-N' cross-coupling interconversion engaging typically inert amide bonds, resulting in a net transamidation process of historically challenging amide bonds. Of the solvents considered, methyl tertbutyl ether (MTBE) and 2-methyltetrahydrofuran (2-MeTHF) were identified as the preferred alternative solvents for the acyl-Buchwald-Hartwig cross-coupling using well-defined and robust Pd(II)-NHC (NHC = N-heterocyclic carbene) precatalysts. MTBE and, in particular, 2-MeTHF are superior solvents in this cross-coupling manifold and recommended in terms of safety, health, biodegradability, and environmental score. The results indicate the replacement of hazardous solvents with green organic solvents in the biorelevant C-N to C-N' cross-coupling manifold of amides to further the burgeoning chemical repertoire of amide-bond activation methods.
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