NU2014-129
INVENTORS
SHORT DESCRIPTION This invention describes a catalytic process for the regioselective 1,2-dearomatization of functionalized azines using an organolanthanide catalyst and pinacolborane (HBpin). It offers a streamlined approach to key intermediates for pharmaceuticals and natural products.
BACKGROUND For decades, precious metal‐based catalysts have dominated organic synthesis, enabling rapid production of pharmaceuticals, natural products, and advanced materials. However, existing dearomatization methods often require harsh reaction conditions and lack selectivity, limiting their efficiency. This invention addresses these challenges by providing an efficient, selective method for the dearomatization of six-membered nitrogen-containing heterocycles, which are critical components in many essential medicines.
ABSTRACT This technology presents a general catalytic approach to achieve regioselective 1,2-dearomatization of functionalized azines using an earth-abundant organolanthanide catalyst in combination with pinacolborane (HBpin). Detailed kinetic studies and computational analyses elucidate the reaction mechanism, establishing the method’s precision and efficiency for preparing valuable synthetic intermediates. The process is designed to meet the needs of commercial synthesis of complex nitrogen-containing compounds, offering robust performance under mild conditions while significantly improving reaction selectivity.
APPLICATIONS
ADVANTAGES
PUBLICATIONS Tobin Marks et al., Atom-Efficient Regioselective 1,2-Dearomatization of Functionalized Pyridines by an Earth-Abundant Organolanthanide Catalyst, Nature Chemistry
IP STATUS Issued US Patent US20160159825A1