96725-18-7Relevant academic research and scientific papers
Hydrodebromination of allylic and benzylic bromides with water catalyzed by a rhodium porphyrin complex
Yang, Wu,Chen, Chen,Chan, Kin Shing
, p. 12879 - 12883 (2018/10/02)
Hydrodebromination of allylic and benzylic bromides was successfully achieved by a rhodium porphyrin complex catalyst using water as the hydrogen source without a sacrificial reductant. Mechanistic investigations suggest that bromine atom abstraction via a rhodium porphyrin metalloradical operates to give the rhodium porphyrin alkyl species and the subsequent hydrolysis of the rhodium porphyrin alkyl species to a hydrocarbon product is a key step to harness the hydrogen from water.
An efficient approach to 2-bromoalken-3-ols by regioselective bromohydroxylation reaction of simple allenes with NBS
Kong, Wangqing,Guo, Binjie,Fu, Chunling,Ma, Shengming
experimental part, p. 2278 - 2285 (2011/06/19)
A regioselective bromohydroxylation reaction of simple allenes affording 2-bromoalken-3-ols in moderate-to-good yields has been developed by using NBS as the electrophilic reagent in a mixture of 1,4-dioxane/H2O (1:1) at room temperature. Throu
1-Bromo-1-lithioethene: A practical reagent in organic synthesis
Novikov, Yehor Y.,Sampson, Paul
, p. 10247 - 10259 (2007/10/03)
A reliable preparative scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -110 °C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Trapping with other electrophiles (acylsilanes, chlorosilanes, tributyltin chloride, iodine) cleanly provides practically useful yields of various 1-substituted 1-bromoethene products. Unexpectedly high diastereoselectivities were observed during the addition of 1-bromo-1- lithioethene to α-siloxy aldehydes (typically 10:1, Felkin-Ahn control) and protected ketopyranose and ketofuranose sugars (> 10:1, addition from the less-hindered face). The title organolithium reagent possesses relatively low basicity at low temperature, and is compatible with a variety of common protecting groups. We believe that these unusual properties of 1-bromo-1-lithioethene may originate from the specific crystalline structure of the reagent in which lithium is coordinatively saturated and thus unavailable for chelation. 2005 American Chemical Society.
1-Bromo-1-lithioethene: A practical reagent for the efficient preparation of 2-bromo-1-alken-3-ols
Novikov, Yehor Y.,Sampson, Paul
, p. 2263 - 2266 (2007/10/03)
(Matrix presented) A reliable preparative-scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -105°C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Efficient diastereoselective addition to α-siloxy and α-methylcyclohexanones, as well as protected 3-keto furanose sugars, is achieved in the presence of 10 mol% CeBr3. The resulting bromoallylic alcohol adducts have considerable potential as synthetic building blocks.
