“…Cheap and structurally simple NaH is one of the most widely used reagents in chemical research. It is generally used as a base in organic synthesis . In sharp contrast, it is rarely used as a reductant or a nucleophile. , In this context, recent elegant studies from the groups of Chiba and Studer reveal such highly sought utility in organic reactions.…”
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.
“…Cheap and structurally simple NaH is one of the most widely used reagents in chemical research. It is generally used as a base in organic synthesis . In sharp contrast, it is rarely used as a reductant or a nucleophile. , In this context, recent elegant studies from the groups of Chiba and Studer reveal such highly sought utility in organic reactions.…”
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.
Herein, a convenient hydrodehalogenation method was described by employing less-explored calcium hydride as the reductant. A wide range of organic halides such as aromatic bromides, aromatic chlorides, aromatic triflates, aliphatic...
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