63122-36-1Relevant academic research and scientific papers
Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides
Zhang, Qing-Bao,Yuan, Pan-Feng,Kai, Liang-Lin,Liu, Kai,Ban, Yong-Liang,Wang, Xue-Yang,Wu, Li-Zhu,Liu, Qiang
supporting information, p. 885 - 889 (2019/02/14)
The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group
Electrochemical oxidative cyclization of olefinic carbonyls with diselenides
Guan, Zhipeng,Wang, Yunkun,Wang, Huamin,Huang, Yange,Wang, Siyuan,Tang, Hongding,Zhang, Heng,Lei, Aiwen
supporting information, p. 4976 - 4980 (2019/09/30)
The tandem cyclization of olefinic carbonyls with easily accessible diselenides facilitated by electrochemical oxidation has been successfully developed, which provides an environmentally friendly method for the construction of C-Se and C-O bonds simultaneously. A series of seleno dihydrofurans and seleno oxazolines, bearing fragile heterocycles, subtle C-I bonds and supernumerary vinyl groups, were forged using this elegant chelation strategy. Neither metal catalysts nor external chemical oxidants are required to promote this transformation.
Electrochemical Fluorocyclization of N-Allylcarboxamides to 2-Oxazolines by Hypervalent Iodine Mediator
Haupt, John D.,Berger, Michael,Waldvogel, Siegfried R.
supporting information, p. 242 - 245 (2019/01/04)
A resource saving protocol for the synthesis of 5-fluoromethyl-2-oxazolines by using electrochemistry has been realized. Thereby, a hypervalent iodine species I(III) is generated by anodic oxidation in the presence of Et3N·5HF and mediates the
Fluorocyclisation via I(I)/I(III) catalysis: A concise route to fluorinated oxazolines
Daniliuc, Constantin G.,Gilmour, Ryan,Kehr, Gerald,Meyer, Stephanie,Scheidt, Felix,Thiehoff, Christian,Yilmaz, Gülay
supporting information, p. 1021 - 1027 (2020/05/06)
Herein, we describe a catalytic fluorooxygenation of readily accessible N-allylcarboxamides via an I(I)/I(III) manifold to generate 2-oxazolines containing a fluoromethyl group. Catalysis is conditional on the oxidation competence of Selectfluor, whilst HF serves as both a fluoride source and Br?nsted acid activator. The C(sp3)–F bond of the mono-fluoromethyl unit and the C(sp3)–O bond of the ring are aligned in a synclinal relationship thereby engaging in stabilising hyperconjugative interactions with vicinal, electron-rich σ-bonds (σC–C→σ*C–F and σC–H→σ*C–O). This manifestation of the stereoelectronic gauche effect was established by X-ray crystallographic analysis of a representative example. Given the importance of fluorine in drug discovery, its ability to modulate conformation, and the prevalence of the 2-oxazoline scaffold in Nature, this strategy provides a rapid entry into an important bioisostere class.
Silver-Promoted Synthesis of 5-[(Pentafluorosulfanyl)methyl]-2-oxazolines
Gilbert, Audrey,Bertrand, Xavier,Paquin, Jean-Fran?ois
supporting information, p. 7257 - 7260 (2018/11/23)
The synthesis of 5-[(pentafluorosulfanyl)methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)propyl]amide to occur without elimination of the chlorine atom, a reaction
Microwave-assisted, Mo(CO)6-mediated, palladium-catalyzed amino-carbonylation of aryl halides using allylamine: from exploration to scale-up
Appukkuttan, Prasad,Axelsson, Linda,der Eycken, Erik Van,Larhed, Mats
, p. 5625 - 5628 (2008/12/22)
Palladium-catalyzed aminocarbonylations of various (hetero)aryl halides with allylamine using Mo(CO)6 as a solid, in situ CO source, were explored. Microwave-enhanced conditions proved to be highly useful in promoting the conversions in a mere 10-20 min with various (hetero)aryl iodides, bromides and chlorides. The scale-up of a microwave-enhanced aminocarbonylation to 25 mmol scale was performed successfully.
The triphenyl phosphite-chlorine reagent in the synthesis of pyrroles from N-allylamides
Spaggiari, Alberto,Vaccari, Daniele,Davoli, Paolo,Prati, Fabio
, p. 995 - 998 (2007/10/03)
A novel application of (PhO)3P-Cl2 chemistry to the synthesis of 2-substituted and 2,3-disubstituted pyrroles from N-allyl-amides is illustrated. A mild procedure is used to generate the imino chloride intermediates, which are subseq
A second generation synthesis of roseophilin and chromophore analogues
Furstner,Gastner,Weintritt
, p. 2361 - 2366 (2007/10/03)
A concise, flexible, and high-yielding synthesis of the macrocyclic compound 4 is outlined which served as a key intermediate in a previous total synthesis of the antitumor active alkaloid roseophilin 1. The key steps of this approach consist of a Pd(0)-catalyzed reaction of vinyloxirane 6 with sulfone 7 and in a subsequent ring closing metathesis (RCM) reaction for the formation of the 13-membered ring catalyzed by the ruthenium carbene Cl2(PCy3)2Ru=CHCH=CPh2 introduced by Grubbs. Moreover, nitrile ylide cycloaddition reactions are used for the preparation of roseophilin side chain mimics. Finally, the synthesis of various chromophore analogues of 1 is reported, including deschlorodesmethoxyroseophilin 12 which is the most elaborate derivative of this complex target reported so far.
