- Synthesis of 9,10-Phenanthrenes via Palladium-Catalyzed Aryne Annulation by o-Halostyrenes and Formal Synthesis of (±)-Tylophorine
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A novel palladium-catalyzed annulation reaction of in situ generated arynes and o-halostyrenes has been developed. This methodology affords moderate to excellent yields of substituted phenanthrenes and is tolerant of a variety of functional groups such as nitrile, ester, amide, and ketone. This annulation chemistry has been successfully applied to the formal total synthesis of a biologically active alkaloid (±)-tylophorine.
- Yao, Tuanli,Zhang, Haiming,Zhao, Yanna
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- Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates
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A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.
- Shao, Jiru,An, Caiyun,Wang, Sunewang R.
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p. 4030 - 4041
(2021/07/19)
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- Organocatalytic cascade reactions for multi-functionalized chiral cyclic ethers through vinylideneortho-quinone methides
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An organocatalytic approach to installing various alcohols into the carbonyl of α,β-unsaturated ketones mediated byVQMintermediates was achieved, followed by dearomatization to provide the stereo-defined cyclic ethersviaa cascade process. Along with the t
- Chang, Yu,Jia, Shiqi,Mao, Hui,Qin, Wenling,Tian, Yuhong,Wang, Pengfei,Yan, Hailong
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supporting information
p. 11334 - 11337
(2021/11/09)
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- Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes
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We demonstrate that aryltriazenes can promote three distinctive types of C-H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. 2-Triazenylbenzaldehydes are shown to be efficient substrates for Rh(I)-catalyzed intermolecular alkyne hydroacylation reactions. The resulting triazene-substituted ketone products can then undergo either a Rh(III)-catalyzed C-H activation, or an electrophilic aromatic substitution reaction, achieving multifunctionalization of the benzene core. Subsequent triazene derivatization provides traceless products.
- Seo, Sangwon,Gao, Ming,Paffenholz, Eva,Willis, Michael C.
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p. 6091 - 6098
(2021/05/29)
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- Domino Synthesis of Thioflavones and Thioflavothiones by Regioselective Ring Opening of Donor-Acceptor Cyclopropane Using In-Situ-Generated Thiolate Anions
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A copper-catalyzed intramolecular ring opening of donor-acceptor cyclopropane is developed for the synthesis of 3-alkyl-carbonated thioflavones and further extended to 3-alkyl-carbonated thioflavothione, using xanthate as a sulfur surrogate. This reaction
- Sundaravelu, Nallappan,Sekar, Govindasamy
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p. 6648 - 6652
(2019/09/07)
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- Palladium Nanoparticles-Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction
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An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2′-iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2′-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. (Figure presented.).
- Parveen, Naziya,Sekar, Govindasamy
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p. 4581 - 4595
(2019/09/03)
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- Enantioselective Intramolecular Reductive Heck Reaction with a Palladium/Monodentate Phosphoramidite Catalyst
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A palladium-catalyzed enantioselective reductive Heck reaction of enones using monodentate phosphoramidite ligands is described. α,α,α’,α’-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL)-based phosphoramidites with palladium(II) acetate, and N-methyl dicy
- Mannathan, Subramaniyan,Raoufmoghaddam, Saeed,Reek, Joost N. H.,de Vries, Johannes G.,Minnaard, Adriaan J.
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p. 551 - 554
(2017/02/26)
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- Ag(i)-catalyzed intramolecular transannulation of enynone tethered donor-acceptor cyclopropanes: A new synthesis of 2,3-dihydronaphtho[1,2-: B] furans
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An efficient AgOTf catalyzed tandem intramolecular transannulation of ((2-alkynyl)aryl)cyclopropyl ketones leading to the 2,3-dihydronaphtho[1,2-b]furans has been developed. The reaction features a regioselective alkyne hydration, cyclopropylketone-2,3-dyhydrofuran rearrangement, and benzannulation. The methodology gives direct access to the tricyclic core structure of biologically important 2,3-dihydronaphtho[1,2-b]furan natural products.
- Dawande, Sudam Ganpat,Harode, Mandeep,Kalepu, Jagadeesh,Katukojvala, Sreenivas
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supporting information
p. 13699 - 13701
(2016/11/29)
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- Palladium-Catalyzed Intermolecular Carbene Insertion Prior to Intramolecular Heck Cyclization: Synthesis of 2-Arylidene-3-aryl-1-indanones
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A domino process that converges the migratory insertion of carbene with a Heck reaction has been established as a versatile tool for the synthesis of 2-arylidene-3-aryl-1-indanones from very stable and easily accessible N-tosylhydrazones and 2′-iodochalco
- Arunprasath, Dhanarajan,Muthupandi, Pandi,Sekar, Govindasamy
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supporting information
p. 5448 - 5451
(2015/11/18)
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- Copper-Catalyzed Domino Synthesis of 2-Arylthiochromanones through Concomitant C-S Bond Formations Using Xanthate as Sulfur Source
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An efficient domino process for the synthesis of thioflavanones has been described using a copper catalyst without addition of any external ligand. A variety of thioflavanones have been synthesized from easily accessible 2′-iodochalcones or 2′-bromochalco
- Sangeetha, Subramani,Muthupandi, Pandi,Sekar, Govindasamy
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supporting information
p. 6006 - 6009
(2016/01/09)
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- COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF
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Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.
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Paragraph 0029
(2013/03/26)
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- A room-temperature, copper-catalyzed cascade process for diethyl 2-aryl-3,4-dihydro-4-oxo-1,1(2 H)-naphthalenedicarboxylate
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A room-temperature cascade process for the formation of diethyl 2-aryl-3,4-dihydro-4-oxo-1,1(2H)-naphthalenedicarboxylate is described by using a combination of Michael addition and copper-catalyzed -arylation of malonic acid derivatives. The protocol worked well for a variety of 1-(2-iodoaryl)enones and displayed great functional group compatibility. Georg Thieme Verlag Stuttgart New York.
- Li, Zhengqiu,Fu, Liangbin,Wei, Jiajia,Ha, Chengyong,Pei, Duanqing,Cai, Qian,Ding, Ke
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experimental part
p. 3289 - 3294
(2010/11/19)
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- Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction
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(Chemical Equation Presented) An efficient intramolecular palladium-catalyzed, asymmetric reductive-Heck reaction has been developed, which allowed for the synthesis of either enantiomerically enriched 3-substituted indanones or α-exo-methylene indanones depending on the base used.
- Minatti, Ana,Zheng, Xiaolai,Buchwald, Stephen L.
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p. 9253 - 9258
(2008/03/13)
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