Chemodivergent Synthesis of One-Carbon-Extended Alcohols via Copper-Catalyzed Hydroxymethylation of Alkynes with Formic Acid
Xin Jin, Hong-Chen Fu, Mei‐Yan Wang, Shouying Huang, Yue Wang, Liang‐Nian He, Xinbin Ma
Abstract
The development of selective catalytic reactions that utilize easily available reagents for the efficient synthesis of alcohols is a long-standing goal of chemical research. Here an intriguing strategy for the chemodivergent copper-catalyzed hydroxymethylation of alkynes with formic acid and hydrosilane has been developed. By simply tuning the amount of formic acid and reaction temperature, distinct one-carbon-extended primary alcohols, that is, allylic alcohols and β-branched alkyl alcohols, were produced with high levels of Z/E-, regio-, and enantioselectivity.
Topics & Concepts
ChemistryFormic acidCatalysisAllylic rearrangementReagentAlkylOrganic chemistryCopperPrimary (astronomy)Carbon fibersAlcoholCombinatorial chemistryComposite numberComposite materialPhysicsAstronomyMaterials scienceCarbon dioxide utilization in catalysisAsymmetric Hydrogenation and CatalysisOrganoboron and organosilicon chemistry