Deoxygenative Geminal Silylboration of Amides Using Silylboronates: Synthesis and Use of α‐Boryl‐α‐Silylalkylamines

Abstract

α‐Silylalkylamines and α‐borylalkylamines are versatile synthetic intermediates and attractive scaffolds found in pharmaceutical drugs and agrochemicals. Despite great progress on synthetic methods for preparation of α‐silylalkylamines or α‐borylalkylamines, there are no general strategies for preparation of α‐boryl‐α‐silylalkylamines and the reactivity has not been explored. Here we report deoxygenative geminal silylboration of amides using silylboronates in the presence of alkoxide base catalyst, producing α‐boryl‐α‐silylalkylamines. The silicon and boron groups in α‐boryl‐α‐silylalkylamines are found to be utilized to chemoselective transformations, such as protonation and alkylation. This protocol serves various α‐silylalkylamines and α‐borylalkylamines from readily available amides.