81585-73-1Relevant academic research and scientific papers
A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions
Wang, Zhihui,Wang, Lei,Wang, Zhiming,Li, Pinhua,Zhang, Yicheng
supporting information, p. 429 - 432 (2020/02/29)
A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.
Metal-free in situ sp3, sp2, and sp C-H functionalization and oxidative cross coupling with benzamidines hydrochloride: A promising approach for the synthesis of α-ketoimides
Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
, p. 60316 - 60326 (2015/02/19)
A new metal-free tandem protocol for the synthesis of α-ketoimides via sp3, sp2, and sp C-H functionalization followed by oxidative cross coupling with benzamidines hydrochloride using catalytic iodine with TBHP in DMSO has been developed. A wide range of functional group tolerance, an inexpensive catalyst, operational simplicity and good to excellent yields of the products are the striking features of this method.
Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes
Donohoe, Timothy J.,Kabeshov, Mikhail A.,Rathi, Akshat H.,Smith, Ian E. D.
experimental part, p. 1093 - 1101 (2012/04/04)
A range of heterocycles, namely thiazoles, imidazoles, imidazopyridines, thiazolidines and dimethoxyindoles, have been synthesised directly from alkenes via a two-step ketoidoination/cyclisation protocol. The alkene starting materials are themselves readily accessible using many different and well-established approaches, and allow access to a variety of heterocycles with excellent yields and regioselectivity.
Oxidative iodination of carbonyl compounds using ammonium iodide and oxone
Marri, Mahender Reddy,MacHarla, Arun Kumar,Peraka, Swamy,Nama, Narender
supporting information; experimental part, p. 6554 - 6559 (2012/01/02)
A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.
Conversion of Aromatic Ketones into α-Arylalkanoic Acids. Oxidation by Thallium(III) and by Halogens
Higgins, Stanley D.,Thomas, Barry C.
, p. 235 - 242 (2007/10/02)
The mechanism by which thallium (III) nitrate oxidises aromatic ketones to α-arylalkanoic acids has been investigated and the role of additives in the system elucidated.It is found that in the absence of additives an organothallium intermediate, most probably the phenacylthallium species BzCH2Tl(NO3)2, persists and that the key to an efficient rearrangement is the ready conversion of this compound into its acetal.Thallium(III) is shown not to be a unique reagent for the oxidation.Other oxidants capable of acting initially as an electrophile and then as a leaving group are equally effective, provided that formation of an acetal is possible.Iodine-silver nitrate in particular offers considerable advantages as reagent over thallium(III).Higher specificity is achieved, unwanted side-reactions can be avoided, and toxicity problems are eliminated.Bromine may be used instead of iodine, but chlorine proves unsatisfactory as an oxidant.
