Sodium Butylated Hydroxytoluene (NaBHT) as a New and Efficient Hydride Source for Pd‐Catalysed Reduction Reactions
| Autor: | Michael G. Organ, Sepideh Sharif, Yu Lu, David Mitchell, Michael John Rodriguez, Michael E. Kopach, Howard N. Hunter |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement 010405 organic chemistry Hydride Aryl Organic Chemistry General Chemistry 010402 general chemistry 01 natural sciences Aldehyde Combinatorial chemistry Redox Catalysis 0104 chemical sciences PEPPSI chemistry.chemical_compound chemistry Butylated hydroxytoluene Methyl group |
| Zdroj: | Chemistry – A European Journal. 25:13099-13103 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.201902876 |
| Popis: | NaBHT (sodium butylated hydroxytoluene), a hindered and soluble base for the efficient arylation of various base-sensitive amines and (hetero)aryl halides has been found to have an unanticipated role as a hydride donor to reduce (hetero)aryl halides and allylic acetates. Mechanistic studies have uncovered that NaBHT, but not BHT, can deliver multiple hydrides through oxidation of the benzylic methyl group in NaBHT to the aldehyde. Further, performing the reduction with NaBHT-d20 has revealed that the redox-active benzylic position is not the only hydride donor site from NaBHT with one hydride in three coming, presumably, from the tert-butyl groups. The reduction works well under mild conditions and, incredibly, only consumes 20 percent of the NaBHT in the process; the remaining 80 percent can be readily recovered in pure form and reused. This, combined with the low cost of the material in ton-scale quantity, makes it practical and attractive for wider use in industry at scale. |
| Databáze: | OpenAIRE |
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