1581275-98-0Relevant articles and documents
Kinetic Study of Carbophilic Lewis Acid Catalyzed Oxyboration and the Noninnocent Role of Sodium Chloride
Johnson, Joel S.,Chong, Eugene,Tu, Kim N.,Blum, Suzanne A.
, p. 655 - 662 (2016)
In the present study, the oxyboration reaction catalyzed by IPrAuTFA in the presence and absence of NaTFA has been examined with kinetic studies, mass spectrometry, and 1H NMR and 11B NMR spectroscopy. Data from monitoring the reacti
Alkoxyboration: Ring-closing addition of B-O σ bonds across alkynes
Hirner, Joshua J.,Faizi, Darius J.,Blum, Suzanne A.
, p. 4740 - 4745 (2014/04/17)
For nearly 70 years, the addition of boron-X σ bonds to carbon-carbon multiple bonds has been employed in the preparation of organoboron reagents. However, the significantly higher strength of boron-oxygen bonds has thus far precluded their activation for addition, preventing a direct route to access a potentially valuable class of oxygen-containing organoboron reagents for divergent synthesis. We herein report the realization of an alkoxyboration reaction, the addition of boron-oxygen σ bonds to alkynes. Functionalized O-heterocyclic boronic acid derivatives are produced using this transformation, which is mild and exhibits broad functional group compatibility. Our results demonstrate activation of this boron-O σ bond using a gold catalysis strategy that is fundamentally different from that used previously for other boron addition reactions.
