1448901-28-7Relevant academic research and scientific papers
Rhodium(I)-catalyzed asymmetric carbene insertion into B-H bonds: Highly enantioselective access to functionalized organoboranes
Chen, Diao,Zhang, Xu,Qi, Wei-Yi,Xu, Bin,Xu, Ming-Hua
, p. 5268 - 5271 (2015)
A unique rhodium(I)-catalyzed asymmetric B-H insertion of α-diazo carbonyl compounds with easily available amine-borane adducts was achieved using a newly developed C1-symmetric chiral diene as ligand. This first Rh(I)-carbene-directed B-H insertion example represents an attractive and promising approach for synthesis of highly enantioenriched organoboron compounds, allowing for the efficient construction of α-boryl esters and ketones with excellent enantioselectivities (up to 99% ee) under exceptionally mild conditions.
N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters
Allen, Thomas H.,Kawamoto, Takuji,Gardner, Sean,Geib, Steven J.,Curran, Dennis P.
, p. 3680 - 3683 (2017)
Boron-hydrogen bond insertion reactions of N-heterocyclic carbene (NHC) boranes and diazoesters can be catalyzed by NHC-boryl iodides and produce stable α-NHC-boryl esters. The conditions of the reaction resemble the previous rhodium-catalyzed transformations (only the catalyst is different); however, the mechanisms of the two reactions are probably very different. The new boryl iodide catalyzed method is adept at producing α-substituted-α-NHC-boryl esters, and this has led to a family of NHC-boryl esters with amino acid and amino-acid-like side chains.
Relative Reactivity of Stable Ligated Boranes and a Borohydride Salt in Rhodium(II)-Catalyzed Boron-Hydrogen Insertion Reactions
Allen, Thomas H.,Curran, Dennis P.
, p. 2094 - 2098 (2016)
Relative reactivities of a series of neutral ligated boranes L-BH3 (where L is NHC, amine, pyridine, or phosphine) and the cyanoborohydride anion have been assessed in Rh(II)-catalyzed B-H insertion reactions with methyl 2-phenyl-2-diazoacetate
Insertion of reactive rhodium carbenes into boron-hydrogen bonds of stable N-heterocyclic carbene boranes
Li, Xiben,Curran, Dennis P.
supporting information, p. 12076 - 12081 (2013/09/02)
Readily available rhodium(II) salts catalyze reactions between NHC-boranes (NHC-BH3) and diazocarbonyl compounds (N2CRCOR′). Stable α-NHC-boryl carbonyl compounds (NHC-BH2-CHRCOR′) are isolated in good yields. The reaction is a reliable way to make boron-carbon bonds with good tolerance for variation in both the NHC-borane and diazocarbonyl components. It presumably occurs by insertion of a transient rhodium carbene into a boron-hydrogen bond of the NHC-borane. Competitive experiments show that a typical NHC-borane is highly reactive toward rhodium carbenes.
