Journal
ACS CATALYSIS
Volume 8, Issue 4, Pages 3016-3020Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b00185
Keywords
sodium hydride; palladium; reduction; debenzylation; deallylation
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Funding
- National Natural Science Foundation of China [21202112, 21738002]
- Suzhou Science and Technology Project [ZXY201435]
- PAPD (A Project - Priority Academic Program Development of Jiangsu Higher Education Institutions)
- Natural Science Foundation of Shandong Province [ZR2016BM07]
- Qingdao Special Research Foundation of Science and Technology [16-1-2-29 nsh]
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Herein we demonstrate simply that the addition of Pd(OAc)(2) as a promotor switches the reactivity of a commonly used base NaH to a nucleophilic reductant. The reactivity is engineered into a palladium-catalyzed reductive debenzylation and deallylation of aryl ethers and esters. This operationally simple, mild protocol displays a broad substrate scope and a broad spectrum of functional group tolerance (>50 examples) and high chemoselectivity toward aryl ethers over aliphatic structures. Moreover, the dual reactivity of NaH as a base and a reductant is demonstrated in efficient synthetic elaboration.
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