Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California, Berkeley, California 94720, United States.
Department of Chemistry, University of California, Berkeley, California 94720, United States.
Org Lett. 2022 Feb 4;24(4):1005-1010. doi: 10.1021/acs.orglett.1c03124. Epub 2022 Jan 26.
We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short- or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.
我们报告了一种脱氢硼化过程，该过程可以与链行走硼氢化反应偶联，从而在一锅、反热力学、短程或长程条件下，将内部烯烃异构化为末端烯烃。这种脱氢硼化通过一个包含活化、碘化和碱促进消除的序列发生。该异构化在室温下进行，不需要氟化物碱，并且该异构化的底物范围比我们以前用硅烷报道的异构化范围更广。
