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Synthesis of selenoether and thioether functionalized bicyclo[1.1.1]pentanes

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Abstract Bicyclo[1.1.1]pentane is widely recognized as the bioisostere for aryl, tert-butyl, and internal alkynes. Herein we report an efficient and practical method for the preparation of selenoether and thioether functionalized… Click to show full abstract

Abstract Bicyclo[1.1.1]pentane is widely recognized as the bioisostere for aryl, tert-butyl, and internal alkynes. Herein we report an efficient and practical method for the preparation of selenoether and thioether functionalized bicyclo[1.1.1]pentanes from selenosulfonates/thiosulfonates and propellane. A variety of valuable bicyclo[1.1.1]pentanes bearing both selenoether/thioether and sulfone are obtained under mild conditions with good yields. The protocol features broad functional group compatibility, excellent atom-economy, simple operation, and gram-scale preparation.

Keywords: bicyclo pentanes; selenoether thioether; functionalized bicyclo; thioether functionalized; synthesis selenoether

Journal Title: Tetrahedron
Year Published: 2020

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