61436-73-5Relevant academic research and scientific papers
Palladium-Catalyzed Alkene Thioacylation: A C?S Bond Activation Approach for Accessing Indanone Derivatives
Wu, Jianing,Xu, Wen-Hua,Lu, Hong,Xu, Peng-Fei
supporting information, p. 3013 - 3017 (2021/05/07)
A palladium-catalyzed intramolecular alkene thioacylation reaction initiated by the activation of thioester C(acyl)?S bonds is reported. This approach successfully suppressed decarbonylation and β-hydrogen elimination with related acyl and alkyl metal thiolate intermediates, providing an efficient and atom-economical method to access indanone scaffolds. Mechanistic studies provide support for C(acyl)?Pd bond insertion of olefins. The synthetic utility of this protocol is demonstrated by the further conversion of the newly formed methylene sulfide substituent. (Figure presented.).
Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts
Bhunia, Samir Kumar,Das, Pritha,Nandi, Shantanu,Jana, Ranjan
supporting information, p. 4632 - 4637 (2019/06/27)
We report herein a visible-light-promoted, highly practical carboxylation of readily accessible aryl triflates at ambient temperature and a balloon pressure of CO2 by the combined use of palladium and photoredox Ir(III) catalysts. Strikingly, the stoichiometric metallic reductant is replaced by a nonmetallic amine reductant providing an environmentally benign carboxylation process. In addition, one-pot synthesis of a carboxylic acid directly from phenol and modification of estrone and concise synthesis of pharmaceutical drugs adapalene and bexarotene have been accomplished via late-stage carboxylation reaction. Furthermore, a parallel decarboxylation-carboxylation reaction has been demonstrated in an H-type closed vessel that is an interesting concept for the strategic sector. Spectroscopic and spectroelectrochemical studies indicated electron transfer from the Ir(III)/DIPEA combination to generate aryl carboxylate and Pd(0) for catalytic turnover.
Visible light driven metal-free intramolecular cyclization: A facile synthesis of 3-position substituted 3,4-dihydroisoquinolin-1(2: H)-one
Zou, Shuai,Geng, Shu,Chen, Lina,Wang, Haitao,Huang, Feng
supporting information, p. 380 - 387 (2019/01/10)
A visible-light metal-free photocatalytic synthesis of 3-position substituted 3,4-dihydroisoquinolin-1(2H)-one derivatives under mild conditions in moderate to good yields is described. EosinY Na, an organic dye, which is of low cost and has good availability, is used as the photocatalyst. A wide range of substrates are tolerated and the gram-scale reaction can also proceed smoothly. Mechanistic studies indicate that a plausible free radical process is proposed.
Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion
Alazet, Sebastien,Preindl, Johannes,Simonet-Davin, Raphael,Nicolai, Stefano,Nanchen, Annik,Meyer, Thierry,Waser, Jerome
, p. 12334 - 12356 (2018/09/27)
Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.
Catalytic Isohypsic-Redox Sequences for the Rapid Generation of Csp3-Containing Heterocycles
Smith, Craig D.,Phillips, David,Tirla, Alina,France, David J.
, p. 17201 - 17204 (2018/11/10)
Cross-coupling reactions catalyzed by transition metals are among the most influential in modern synthetic chemistry. The vast majority of transition-metal-catalyzed cross-couplings rely on a catalytic cycle involving alternating oxidation and reduction o
Catalytic C-N and C-H Bond Activation: Ortho-Allylation of Benzoic Acids with Allyl Amines
Hu, Xiao-Qiang,Hu, Zhiyong,Zhang, Guodong,Sivendran, Nardana,Goo?en, Lukas J.
supporting information, p. 4337 - 4340 (2018/07/29)
A facile insertion of ruthenium into aromatic C-H and allylic C-N bonds are the key steps in a [Ru(p-cymene)Cl2]2-catalyzed ortho-C-H allylation of benzoic acids. This protocol allows drawing on the large pool of allylic amines for state-of-the-art ortho-functionalizations of arenes, turning neutral amines into leaving groups. Concise syntheses of biologically active compounds provide further evidence of the synthetic potential of this methodology.
Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents
Alazet, Sébastien,Le Vaillant, Franck,Nicolai, Stefano,Courant, Thibaut,Waser, Jerome
supporting information, p. 9501 - 9504 (2017/07/22)
A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.
Intramolecular Hydroamidation of ortho-Vinyl Benzamides Promoted by Potassium tert-Butoxide/N,N-Dimethylformamide
Chen, Zhen-Yu,Wu, Liang-Yu,Fang, Hai-Sheng,Zhang, Ting,Mao, Zhi-Feng,Zou, Yong,Zhang, Xue-Jing,Yan, Ming
, p. 3894 - 3899 (2017/10/07)
An intramolecular hydroamidation of ortho-vinyl benzamides had been developed. The reaction was promoted efficiently by potassium tert-butoxide and N,N-dimethylformamide without the need for strong oxidants or transition-metal catalysts. A series of dihyd
Direct oxidative lactonization of alkenoic acids mediated solely by NaIO4: Beyond a simple oxidant
Kang, Yan-Biao,Chen, Xian-Min,Yao, Chuan-Zhi,Ning, Xiao-Shan
supporting information, p. 6193 - 6196 (2016/05/19)
Triflic acid-catalyzed direct oxidative lactonization of alkenoic acids mediated solely by NaIO4 without halogen salts is described. Sodium periodate works not only as an oxidant, but also as an active reagent and directly mediates the lactonization. A new cheap, green, and practical oxidative lactonization approach has been developed using NaIO4 as the sole reagent.
Direct carbocyclizations of benzoic acids: Catalyst-controlled synthesis of cyclic ketones and the development of tandem aHH (acyl Heck-Heck) reactions
Miles, Kelsey C.,Le, Chi,Stambuli, James P.
supporting information, p. 11336 - 11339 (2014/10/16)
The formation of exo-methylene indanones and indenones from simple ortho-allyl benzoic acid derivatives has been developed. Selective formation of the indanone or indenone products in these reactions is controlled by choice of ancillary ligand. This new process has a low environmental footprint as the products are formed in high yields using low catalyst loadings, while the only stoichiometric chemical waste generated from the reactants in the transformation is acetic acid. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction, and utilized in the synthesis of donepezil. Carboxylic acids in aHH: Simple ortho-allyl benzoic acid derivatives have been utilized in an acyl Heck (aH) reaction to selectively form indanones and indenones. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction to form two sp 2-sp2 bonds of (E)-trisubstituted olefins.
