Divergent Synthesis of 1,1-Carbonyl Amino Alkyl Borons from Indoles

Abstract

α-Boryl carbonyl species and α-boryl amino compounds are valuable and important frameworks in organic synthesis. However, the strategies that could merge the two scaffolds into one compound, named 1,1-carbonyl amino alkyl boron, are elusive and underdeveloped. Herein, we present an efficient method that could address this gap and produce 1,1-carbonyl amino alkyl borons from readily accessible indoles via oxidation by m-CPBA or oxone. This reaction features operational simplicity, divergent synthesis, broad substrate scope, and valuable products.

Photoinduced catalyst-free borylation of alkenyl triflates with Lewis base complexes of boranes

“…4 Thus, many Lewis base-ligated boranes (LB-BH 3 ) 5 have been identified and utilized to access isolable α-borylcarbonyl scaffolds. 6 Among them, transition-metal catalysed direct borylation of α-diazocarbonyl compounds with LB-BH 3 provided a route to α-borylcarbonyl compounds, but the diazo starting materials are difficult to prepare due to safety concerns. 7 Alternatively, terminal alkynes and sulfoxonium ylides have also been demonstrated to be suitable coupling partners to react with LB-BH 3 for the synthesis of α-borylcarbonyl compounds.…”