81097-24-7Relevant academic research and scientific papers
Aza-heterocycles via copper-catalyzed, remote C–H desaturation of amines
Dare, Ross M.,Nagib, David A.,Paneque, Alyson N.,Stateman, Leah M.
supporting information, p. 210 - 224 (2022/01/19)
A majority of medicines contain a nitrogen atom within a five- or six-membered ring. To rapidly access both such aza-heterocycles, we sought to develop a remote C–H desaturation of amines. Inspired by the Hofmann-L?ffler-Freytag (HLF) synthesis of five-me
Rhodium(III)-Catalyzed Synthesis of Skipped Enynes via C(sp3)–H Alkynylation of Terminal Alkenes
Della-Felice, Franco,Zanini, Margherita,Jie, Xiaoming,Tan, Eric,Echavarren, Antonio M.
supporting information, p. 5693 - 5698 (2021/02/09)
The RhIII-catalyzed allylic C?H alkynylation of non-activated terminal alkenes leads selectively to linear 1,4-enynes at room-temperature. The catalytic system tolerates a wide range of functional groups without competing functionalization at other positions. Similarly, the vinylic C?H alkynylation of α,β- and β,γ- unsaturated amides gives conjugated Z-1,3-enynes and E-enediynes.
Au(I)-Catalyzed Oxidative Functionalization of Yndiamides
Tong, Zixuan,Garry, Olivia L.,Smith, Philip J.,Jiang, Yubo,Mansfield, Steven J.,Anderson, Edward A.
supporting information, p. 4888 - 4892 (2021/06/28)
Yndiamides, underexplored cousins of ynamides, offer rich synthetic potential as doubly nitrogenated two carbon building blocks. Here we report a gold-catalyzed oxidative functionalization of yndiamides to access unnatural amino acid derivatives, using a wide range of nucleophiles as a source of the amino acid side chain. The transformation proceeds under mild conditions, is highly functional group tolerant, and displays excellent regioselectivity through subtle steric differentiation of the yndiamide nitrogen atom substituents.
Practical Synthesis of Halogenated N-Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes
He, Xinxu,He, Yanyang,Qin, Xiaowen,Wu, Xiao-Feng,Yin, Zhiping
supporting information, p. 5831 - 5834 (2021/11/17)
A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.
A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization
Li, Sifan,Wang, Yu,Wu, Zibo,Shi, Weiliang,Lei, Yibo,Davies, Paul W.,Shu, Wei
supporting information, p. 7209 - 7214 (2021/09/14)
Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.
Highly selective hydrosilylation of equilibrating allylic azides
Liu, Ruzhang,Liu, Yongmei,Wang, Juan,Wei, Zhen,Xue, Huaiguo
supporting information, p. 5038 - 5041 (2020/05/18)
The Pt-catalyzed hydrosilylation of equilibrating allylic azides is reported. The reaction provides only one out of four possible hydrosilylation products in good yields and with very high chemoselectivity (alk-1-enevs.alk-2-ene), regioselectivity (linearvs.branched), and excellent functional group tolerance.
Synthesis method of 3-azidopropylsilane
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Paragraph 0086; 0087, (2020/06/05)
The invention discloses a synthetic method of 3-azidopropylsilane, wherein the method comprises the steps: firstly, allyl azide is synthesized by allyl bromide, and because the allyl azide is easy togenerate [3,3] rearrangement reaction at room temperatur
Copper-Catalyzed Carbonylative Synthesis of β-Homoprolines from N-Fluoro-sulfonamides
Wu, Xiao-Feng,Yin, Zhiping,Zhang, Youcan
supporting information, p. 1889 - 1893 (2020/03/24)
A new methodology for the carbonylative transformation of N-fluoro-sulfonamides into N-sulfonyl-β-homoproline esters has been described. In the presence of a catalytic amount of Cu(OTf)2, a range of β-homoproline derivatives were prepared in moderate to good yield. The reaction proceeds via the intramolecular cyclization and intermolecular carbonylation of a free carbon radical. Notably, this procedure offers the possibility to build potential functionalized bioactive molecules.
Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π-Alkene Activation
Amgoune, Abderrahmane,Bourissou, Didier,Rigoulet, Mathilde,Thillaye du Boullay, Olivier
supporting information, p. 16625 - 16630 (2020/07/24)
Heteroarylation of alkenes with aryl iodides was efficiently achieved with a (MeDalphos)AuCl complex through AuI/AuIII catalysis. The possibility to combine oxidative addition of aryl iodides and π-activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5-, 6-, and 7-membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron-rich aryl substrates, which are troublesome with alternative photoredox/oxidative approaches. In addition, it provides a very unusual switch in regioselectivity from 5-exo to 6-endo cyclization between the Z and E isomers of internal alkenols.
CpTiCl2-Catalyzed Cross-Coupling between Internal Alkynes and Ketones: A Novel Concept in the Synthesis of Halogenated, Conjugated Dienes
Roldan-Molina, Esther,Nievas, Maria M.,Navarro, Jorge A. R.,Oltra, J. Enrique
supporting information, p. 8296 - 8301 (2020/06/17)
A novel concept for the synthesis of halogenated, conjugated dienes is disclosed: the CpTiCl2-catalyzed coupling of keto-alkynes, in the presence of Me3SiBr/Et3N?HBr. This reaction provided five-, six-, and seven-membered
