Sodium-Metal-Promoted Reductive 1,2-<i>syn</i>-Diboration of Alkynes with Reduction-Resistant Trimethoxyborane
Shiori Ito, Mizuki Fukazawa, Fumiya Takahashi, Keisuke Nogi, Hideki Yorimitsu
Abstract
Abstract Reductive 1,2-diboration of alkynes has been accomplished by means of sodium dispersion in the presence of trimethoxyborane as a reduction-resistant boron electrophile. Two boron moieties can be introduced onto alkynes with excellent syn selectivity to afford the corresponding (Z)-1,2-diborylalkenes. Bis(borate) species generated in situ can be involved in one-pot Suzuki-Miyaura arylation, formal arylboration of alkynes thus being executed.
Topics & Concepts
ChemistryReduction (mathematics)Reductive eliminationMetalSodiumMedicinal chemistryOrganic chemistryCatalysisMathematicsGeometryOrganoboron and organosilicon chemistryBoron Compounds in ChemistryChemical Synthesis and Analysis