6341-56-6Relevant articles and documents
Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates
Ji, Xiaolei,Shen, Chaoren,Tian, Xinxin,Dong, Kaiwu
, p. 8645 - 8649 (2021/10/25)
A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.
Palladium-catalyzed cascade synthesis of spirocyclic oxindoles via regioselective C2-H arylation and C8-H alkylation of naphthalene ring
Luo, Xiai,Li, Wenguang,Lu, Haiyan,Deng, Guobo,Yang, Yuan,Yang, Chunming,Liang, Yun
supporting information, p. 713 - 716 (2020/07/24)
A simultaneous C2-H arylation and C8-H alkylation of naphthalene ring has been achieved by palladium-catalyzed cascade reaction of N-(2-halophenyl)-2-(naphthalen-1-yl)acrylamides with aryl iodides, which provides an efficient method for synthesizing various aryl-substituted spirocyclic oxindoles. The protocol enables three C–C bonds formation via an intramolecular Heck reaction and sequentially regioselective C–H bond activation.
Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates
Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
supporting information, p. 5054 - 5059 (2021/07/20)
An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.
Cobalt-Catalyzed Vinylic C-H Addition to Formaldehyde: Synthesis of Butenolides from Acrylic Acids and HCHO
Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
supporting information, p. 8359 - 8364 (2021/11/01)
A carboxyl-assisted C-H functionalization of acrylic acids with formaldehyde to give butenolides is described. It is the first time that the addition of an inert vinylic C-H bond to formaldehyde has been achieved via cobalt-catalyzed C-H activation. The unique reactivity of the cobalt species was observed when compared with related Rh or Ir catalysts. γ-Hydroxymethylated butenolides were produced by the treatment of Na2CO3 after the catalytic reaction in one pot.
Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides
Coles, Simon J.,Hareram, Mishra Deepak,Harnedy, James,Morrill, Louis C.,Tizzard, Graham J.
supporting information, p. 12643 - 12646 (2021/12/07)
An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.
Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions
Goh, Jeffrey,Loh, Teck-Peng,Maraswami, Manikantha
supporting information, p. 9724 - 9728 (2020/12/21)
Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.
Palladium-Catalyzed Highly Regioselective Hydrocarboxylation of Alkynes with Carbon Dioxide
Chen, Pengquan,Cheng, Ruixiang,Jiang, Huanfeng,Lei, Ming,Lou, Hongming,Qi, Chaorong,Shi, Fuxing,Wang, Lu,Wu, Wanqing,Xiong, Wenfang,Zhu, Baiyao
, p. 7968 - 7978 (2020/08/21)
A Pd-catalyzed highly regioselective hydrocarboxylation of alkynes with carbon dioxide has been established. By the combination of Pd(PPh3)4 and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (binap), a variety of functionalized alkynes, including aryl alkynes, aliphatic alkynes, propargylamines, and propargyl ethers, could be leveraged to provide a wide array of α-acrylic acids in high yields with high regioselectivity under mild reaction conditions. Experimental and DFT mechanistic studies revealed that this reaction proceeded via the cyclopalladation process of alkynes and carbon dioxide in the presence of binap to generate a five-membered palladalactone intermediate and enabled the formation of Markovnikov adducts. Moreover, this strategy provided an effective method for the late-stage functionalization of alkyne-containing complicated molecules, including natural products and pharmaceuticals.
A 1,3,2-Diazaphospholene-Catalyzed Reductive Claisen Rearrangement
Reed, John H.,Donets, Pavel A.,Miaskiewicz, Solène,Cramer, Nicolai
supporting information, p. 8893 - 8897 (2019/05/28)
1,3,2-Diazaphospholenes (DAPs) are an emerging class of organic hydrides. In this work, we exploited them as efficient catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature. Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O-bound phospholene enolates and provide a proof-of-principle for catalytic enantioselective reactions.
Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes
Jiang, Bing,Zhao, Meng,Li, Shu-Sen,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 555 - 559 (2018/02/21)
A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3-conjugated diene structure.
Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes
Song, Shengjin,Lu, Ping,Liu, Huan,Cai, Sai-Hu,Feng, Chao,Loh, Teck-Peng
, p. 2869 - 2872 (2017/06/13)
A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.
