202974-92-3Relevant academic research and scientific papers
Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications
Engl, Sebastian,Reiser, Oliver
, p. 5581 - 5586 (2021/07/26)
Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.
Transition-Metal-Free One-Step Synthesis of Ynamides
Zeng, Xianzhu,Tu, Yongliang,Zhang, Zhenming,You, Changming,Wu, Jiao,Ye, Zhiying,Zhao, Junfeng
, p. 4458 - 4466 (2019/03/26)
A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.
Selective 7- endo -Cyclization of 3-Aza-5-alkenols through Oxidative Pd(II)-Catalyzed Olefin Oxyarylation
Gazzola, Silvia,Beccalli, Egle M.,Borelli, Tea,Castellano, Carlo,Diamante, Daria,Broggini, Gianluigi
, p. 503 - 508 (2017/11/16)
3-Aza-5-alkenols undergo selective 7- endo - trig cyclization when treated with a catalytic Pd(II) species, CuCl 2 and ArSnBu 3 giving 7-aryl-substituted oxazepanes. The intramolecular alkoxylation occurs with formation of a seven-me
General Strategy for Stereoselective Synthesis of β- N-Glycosyl Sulfonamides via Palladium-Catalyzed Glycosylation
Dai, Yuanwei,Zheng, Jianfeng,Zhang, Qiang
supporting information, p. 3923 - 3927 (2018/07/21)
A highly efficient and mild glycosylation reaction between 3,4-O-carbonate glycal and N-tosyl functionalized aliphatic and aromatic amines via palladium-catalyzed decarboxylative allylation is disclosed. A wide range of highly functionalized 2,3-unsaturat
Enantioselective Synthesis of trans-Vicinal Diamines via Rhodium-Catalyzed [2+2] Cycloaddition of Allenamides
Zheng, Wei-Feng,Sun, Gui-Jun,Chen, Liang,Kang, Qiang
supporting information, p. 1790 - 1794 (2018/04/02)
An efficient protocol for the enantioselective Rh-catalyzed intermolecular head-to-head [2+2] cycloaddition of allenamides was developed. A variety of enantio-enriched cyclobutane-1,2-diamine derivatives were achieved in good yields with good to excellent enantioselectivities. (Figure presented.).
Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)5 and Phenanthroline System
Hwang, Joon Young,Baek, Jong Hwa,Shin, Tae Il,Shin, Jung Ha,Oh, Jae Won,Kim, Kwang Pyo,You, Youngmin,Kang, Eun Joo
, p. 4900 - 4903 (2016/10/18)
An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)5] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)5, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.
Ynamide Carbopalladation: A Flexible Route to Mono-, Bi- and Tricyclic Azacycles
Campbell, Craig D.,Greenaway, Rebecca L.,Holton, Oliver T.,Walker, P. Ross,Chapman, Helen A.,Russell, C. Adam,Carr, Greg,Thomson, Amber L.,Anderson, Edward A.
, p. 12627 - 12639 (2015/09/01)
Bromoenynamides represent precursors to a diversity of azacycles by a cascade sequence of carbopalladation followed by cross-coupling/electrocyclization, or reduction processes. Full details of our investigations into intramolecular ynamide carbopalladation are disclosed, which include the first examples of carbopalladation/cross-coupling reactions using potassium organotrifluoroborate salts; and an understanding of factors influencing the success of these processes, including ring size, and the nature of the coupling partner. Additional mechanistic observations are reported, such as the isolation of triene intermediates for electrocyclization. A variety of hetero-Diels-Alder reactions using the product heterocycles are also described, which provide insight into Diels-Alder regioselectivity.
Extending the stetter reaction with 1,6-acceptors
Law, Katherine R.,McErlean, Christopher S. P.
, p. 15852 - 15855 (2014/04/03)
Pace Stetter: A new N-heterocyclic carbene (NHC)-catalysed transformation is described-the intramolecular vinylogous Stetter reaction. This transformation can be effected with both thiazolium and triazolium-based catalysts, using aromatic and aliphatic aldehydes, employing α,β,γ,δ- unsaturated esters, ketones, phosphonates and N-acylpyrroles, and can be conducted enantioselectively (see scheme). Copyright
Reductive cyclization of bromoenynamides with alcohols as hydride source: Synthesis and reactions of 2-amidodienes
Greenaway, Rebecca L.,Campbell, Craig D.,Chapman, Helen A.,Anderson, Edward A.
supporting information, p. 3187 - 3194 (2013/01/15)
Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium-catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5-8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, alkynes and arynes) under various conditions gives bi- and tricyclic azacycles, which can be further oxidized to the aromatic azacycles. Copyright
Gold-catalyzed direct activation of allylic alcohols in the stereoselective synthesis of functionalized 2-vinyl-morpholines
Bandini, Marco,Monari, Magda,Romaniello, Alessandro,Tragni, Michele
, p. 14272 - 14277 (2011/03/19)
Alcohol versus alcohol: A highly stereocontrolled synthesis of substituted morpholines is realized by means of gold-catalyzed dehydrative allylic cyclization of diols (see scheme for one example; segphos = 5,5′-bis[di(3, 5-di-tert-butyl-4-methyoxyphenyl)phosphine]-4,4′-bi-1,3-benzodioxole). The present methodology represents one of the few examples of enantioselective gold-catalyzed transformations involving unactivated alkenes. Copyright
