Asymmetric Borylation of Remote C(sp3)-H Bonds for the Construction of Compounds with Three-Dimensional Structural Diversity

2022 Fiscal Year Annual Research Report

• Project/Area Number: 20K15269
• Research Institution: Hokkaido University
• Principal Investigator: REYES RONALD・LAZO 北海道大学, 化学反応創成研究拠点, 特任助教 (30845475)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: borylation / asymmetric synthesis

Outline of Annual Research Achievements

With our interest in the development of novel methodologies for the transformation of C-H bonds in readily available feedstock chemicals, we previously demonstrated the competent activation and subsequent asymmetric borylation of g-C(sp3)-H bonds under Ir catalysis. Our collaboration with ICReDD scientists has given us infinite opportunity to further extend the reactivity of our catalytic system. Thus, guided by calculation derived transition-state models, we recently succeeded in the asymmetric borylation of more distal C-H bonds in the aliphatic hydrocarbon chain of common and readily available chemical feedstocks including biomass resources allowing for a more sustainable and efficient organic synthesis. Thereby, the borylation of e-C-H bonds, located five carbons away from the carbonyl group of the substrate, has been achieved - a direct functionalization realized using a modularly designed supramolecular catalytic assembly.