68267-69-6Relevant articles and documents
Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor
Chang, Zhe,Dong, Zheng,Ma, Tong,Zhang, Yu,Zhao, Depeng,Zhao, Heng
supporting information, (2020/03/19)
We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.
Aerobic intramolecular aminothiocyanation of unactivated alkenes promoted by in situ generated iodine thiocyanate
Feng, Yangyang,Hussain, Muhammad Ijaz,Zhang, Xiaohui,Shi, Jian,Hu, Wen,Xiong, Yan
, p. 2669 - 2676 (2018/05/04)
Aerobic intramolecular aminothiocyanation of unactivated alkenes has been developed by in situ generated iodine thiocyanate under open-flask conditions. This protocol provides a concise and efficient method for synthesizing SCN-containing pyrrolidine, piperidine and indoline derivatives with isolated yields of up to 87%. Furthermore, mixing iodine and sodium thiocyanate with oxygen afforded iodine thiocyanate (ISCN) and dithiocyanatoiodate [I(SCN)2]- which were testified by liquid chromatography mass spectrometry. A mechanistic investigation indicates that iodonium ion and sulfonium ion intermediates might be involved in this transformation.
2-(Phenylseleno)ethanesulfon-amide as a novel protecting group for aniline that can be deprotected by a radical reaction
Kihara, Nobuhiro,Mitsuhashi, Yuji,Sato, Makoto,Hirose, Shun-Ichi,Goudo, Erika,Uzawa, Yoshinori,Shirai, Natsumi,Hamamoto, Sari,Iwasaki, Ryo,Fujioka, Akane
, p. 2563 - 2566 (2016/06/06)
Anilines were protected as 2-(phenylseleno)ethanesulfonanilide (SeES anilide) via sulfonylation by 2-chlorosulfonyl chloride followed by the conjugate addition of benzeneselenol. The SeES anilide was deprotected by radical reduction using tributyltin hydride in the presence of AIBN. The corresponding anilines were obtained in high yields when the hydride and AIBN were added to the system slowly. Since the radical reaction proceeds under neutral conditions, chemoselective deprotection of the SeES group was accomplished. The SeES anilide was stable under various conditions, including some severe conditions.
Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate
Li, Jiaming,Grubbs, Robert H.,Stoltz, Brian M.
, p. 5449 - 5451 (2016/11/17)
A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.
Bond-Weakening Catalysis: Conjugate Aminations Enabled by the Soft Homolysis of Strong N-H Bonds
Tarantino, Kyle T.,Miller, David C.,Callon, Ted A.,Knowles, Robert R.
supporting information, p. 6440 - 6443 (2015/06/08)
The ability of redox-active metal centers to weaken the bonds in associated ligands is well precedented, but has rarely been utilized as a mechanism of substrate activation in catalysis. Here we describe a catalytic bond-weakening protocol for conjugate a
Palladium(II)-catalyzed intramolecular tandem aminoalkylation via divergent C(sp3)-H functionalization
Du, Wei,Gu, Qiangshuai,Li, Zhongliang,Yang, Dan
supporting information, p. 1130 - 1135 (2015/02/05)
(Chemical Equation Presented) We have developed a Pd(II)-catalyzed oxidative tandem aminoalkylation via divergent C(sp3)-H functionalization, a ffording three- and five-membered-ring fused indolines in good yields under two optimized conditions, respectively. The mechanism studies have indicated that the benzylic C - H cleavage involved in the former transformation is the rate-determining step, while the cleavage of amide α-C - H in the latter is not. This is the first example of a Pd-catalyzed tandem reaction involving C(sp3)-H activation without the employment of prefunctionalized reagents (e.g., halogenated and boron reagents) and directing groups, representing a green and economic protocol for the construction of N-containing heterocycles.
Cu(oac)2-promoted cascade carboamination/oxidative cyclization of c-acylimines with alkenes
Dang, Ling,Liang, Libo,Qian, Cheng,Fu, Meiqin,Ma, Tongmei,Xu, Dingguo,Jiang, Huanfeng,Zeng, Wei
, p. 769 - 776 (2014/04/03)
A Cu(OAc)2-promoted cascade carboamination/oxidative cyclization of alkenes with a-imino esters has been explored. This transformation provides a concise approach to rapid assembly of 2-oxo-3-iminopyrrole derivatives in moderate to good yields.
Rh(III)-catalyzed tandem C-H allylation and oxidative cyclization of anilides: A new entry to indoles
Cajaraville, Ana,Lopez, Susana,Varela, Jesus A.,Saa, Carlos
supporting information, p. 4576 - 4579 (2013/09/24)
RhIII-catalyzed tandem C-H allylation and oxidative cyclization of anilides with allyl carbonates in the presence of a slight excess of AgSbF6 salt and Cu(OAc)2 as oxidant affords easy, economical access to important bioac
Palladium(II)-catalyzed oxidative cascade cyclization reactions of anilides and anilines: Scope and mechanistic investigations
Yip, Kai-Tai,Yang, Dan
, p. 2166 - 2175 (2011/10/12)
With Pd(OAc)2/pyridine as the catalyst system and molecular oxygen as a green oxidant, acrylanilides and N-allylanilines undergo oxidative cascade cyclization to form heterocyclic rings in high yields. This methodology is applicable to acrylani
The attempted stereoselective synthesis of chiral 2,2′-biindoline
Gresser, Mary J.,Wales, Steven M.,Keller, Paul A.
experimental part, p. 6965 - 6976 (2010/09/18)
The attempted first stereoselective synthesis of 2,2′-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the he
