15642-89-4Relevant academic research and scientific papers
ZnI2/NaCNBH3 as an Efficient Reagent for Regioselective Ring Opening of the Benzylic Epoxide Moiety
Finkielsztein,Aguirre,Lantano,Alesso,Moltrasio Iglesias
, p. 895 - 901 (2004)
In the presence of zinc iodide, sodium cyanoborohydride was found to produce regioselective ring opening of benzylic epoxides in mild reaction conditions.
Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
Von Keutz, Timo,Cantillo, David,Kappe, C. Oliver
supporting information, p. 7537 - 7541 (2020/10/12)
The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).
Cascade bio-hydroxylation and dehalogenation for one-pot enantioselective synthesis of optically active β-halohydrins from halohydrocarbons
Cui, Hai-Bo,Xie, Ling-Zhi,Wan, Nan-Wei,He, Qing,Li, Zhi,Chen, Yong-Zheng
supporting information, p. 4324 - 4328 (2019/08/21)
A stereoselective hydroxylation and enantioselective dehalogenation cascade reaction was developed for the synthesis of optically active β-haloalcohols from halohydrocarbons. This cascade system employed P450 and halohydrin dehalogenase as two compatible biocatalysts, allowing a straightforward, greener and efficient access to β-halohydrins with excellent enantioselectivities (98-99%).
The vicinal functionalization of olefins: A facile route to the direct synthesis of β-chlorohydrins and β-chloroethers
Swamy, Peraka,Kumar, Macharla Arun,Reddy, Marri Mahender,Naresh, Mameda,Srujana, Kodumuri,Narender, Nama
, p. 26288 - 26294 (2014/07/08)
An efficient and environmentally benign protocol for the synthesis of vicinal chlorohydroxy and chloromethoxy derivatives in a highly regioselective manner from olefins using NH4Cl as a chlorine source and oxone as an oxidant in aqueous acetone and methanol is demonstrated. This methodology offers an additive and metal chloride free approach and is endowed with simple reaction conditions, high yields a broad substrate scope and good functional group tolerance. Moreover, the aromatic substrates with a terminal double bond exhibited merely Markovnikov selectivity, while the internal alkenes show exclusive regiocontrol and low to moderate diastereoselectivity.
Efficient synthesis of chlorohydrins using ClCH2MgCl·LiCl
Nishimura, Rodolfo H.V.,Toledo, Fabiano T.,Lopes, Jo?o L.C.,Clososki, Giuliano C.
, p. 287 - 290 (2013/02/23)
The mixed lithium-magnesium carbenoid ClCH2MgCl·LiCl was easily generated in THF through the reaction of chloroiodomethane with i-PrMgCl·LiCl at -78 °C. This reagent reacts well with a number of aldehydes to give the corresponding chlorohydrins in good yields.
Highly regio- and diastereoselective halohydroxylation of olefins: A facile synthesis of vicinal halohydrins
Zhang, Jinglei,Wang, Jie,Qiu, Zhuibai,Wang, Yang
experimental part, p. 6859 - 6867 (2011/10/02)
An efficient method for the synthesis of vicinal chlorohydrin or bromohydrin derivatives has been developed on the basis of direct halohydroxylation of various olefins with electrondonating or withdrawing substituent. The reactions were carried out under mild conditions in the presence of N-tosyl-l-threonine (NTsLT) as an acidic additive using chloramine T trihydrate, 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) or N-bromoacetamide (AcNHBr) as the halogen source, respectively, affording the corresponding vicinal halohydrins in good to high yields with excellent regio- and stereoselectivities.
Thiourea catalysis of NCS in the synthesis of chlorohydrins
Bentley, Paul A.,Mei, Yujiang,Du, Juan
, p. 1425 - 1427 (2008/09/18)
Thiourea catalysis of reactions utilizing N-succinimides is demonstrated with NCS chlorination of olefins in the presence of water to afford chlorohydrins.
Highly efficient route for enantioselective preparation of chlorohydrins via dynamic kinetic resolution
Traeft, Annika,Bogar, Krisztian,Warner, Madeleine,Baeckvall, Jan-E.
supporting information; experimental part, p. 4807 - 4810 (2009/05/31)
(Equation Presented) Dynamic kinetic resolution (DKR) of various aromatic chlorohydrins with the use of Pseudomonas cepacia lipase (PS-C "Amano" II) and ruthenium catalyst 1 afforded chlorohydrin acetates in high yields and high enantiomeric excesses. These optically pure chlorohydrin acetates are useful synthetic intermediates and can be transformed to a range of important chiral compounds.
Method of producing ethynyl aromatic compounds
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, (2008/06/13)
The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conduct
