Affiliation:
1. KAUST Catalysis Center (KCC) King Abdullah University of Science and Technology (KAUST) Thuwal 23955-6900 Saudi Arabia
2. Eastern Institute for Advanced Study Eastern Institute of Technology Ningbo 315200 China
3. Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry Fuzhou University Fuzhou 350108 China
Abstract
AbstractThe difunctionalization of unsaturated bonds plays a vital role in the enrichment of molecular complexity. While various catalytic methods for alkene and alkyne difunctionalization have been developed in recent years, hetero‐functionalization the introduction of two different atoms has been less explored. This is mainly due to the challenges associated with achieving high chemo‐, regio‐, and stereoselectivity, especially when adding two similar atoms from the same group across unsaturated bonds. In this study, we describe a nickel‐catalyzed, three‐component reductive protocol for group 14 element hetero‐difunctionalization of 1,3‐enynes using electrochemistry. This new method is mild, selective, and general, allowing for the silyl‐, germanyl‐, and stannyl‐alkylation of enynes. Various chlorosilanes as well as chlorogermans, and chlorostannanes can be successfully used in combination with aryl/alkyl‐substituted 1,3‐enynes and primary, secondary, and tertiary alkyl bromides in the electroreductive coupling.
Funder
Global Collaborative Research, King Abdullah University of Science and Technology