170956-92-0Relevant articles and documents
Copper-catalyzed aerobic oxidative carbocyclization-ketonization cascade: Selective synthesis of quinolinones
Xie, Peng,Wang, Zhi-Qiang,Deng, Guo-Bo,Song, Ren-Jie,Xia, Jia-Dong,Hu, Ming,Li, Jin-Heng
, p. 2257 - 2262 (2013)
A new thematic extension method is described for the carbocyclization of α-C(sp3)-H bonds of amides with alkynes followed by ketonization of the alkynes that utilizes the inexpensive copper(II) acetoacetonate [Cu(acac)2] as catalyst
Visible-Light-Mediated [2+2+1] Carbocyclization Reactions of 1,7-Enynes with Bromofluoroacetate to Form Fused Monofluorinated Cyclopenta[ c]quinolin-4-ones
Li, Yongqiang,Liu, Yuxiu,Qu, Yi,Song, Hongjian,Wang, Qingmin,Xu, Wentao,Zhang, Jingjing
, p. 5379 - 5389 (2020/05/19)
Herein, we describe a new protocol for photoinduced radical [2+2+1] carbocyclization reactions of 1,7-enynes with bromofluoroacetate. These reactions, which proceed via a cascade involving fluoroalkylation, 6-exo-dig and 5-endo-trig cyclizations, H-transf
Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
Liang, Hao,He, Xiaobo,Zhang, Yaqi,Chen, Bin,Ouyang, Jia-Sheng,Li, Yongsu,Pan, Bendu,Subba Reddy, Chitreddy V.,Chan, Wesley Ting Kwok,Qiu, Liqin
supporting information, p. 11429 - 11432 (2020/10/12)
The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz
B(C6F5)3-Catalyzed cyclization of alkynes: direct synthesis of 3-silyl heterocyclic compounds
Li, Mengxing,Wang, Ting,An, Zhenyu,Yan, Rulong
supporting information, p. 11953 - 11956 (2020/10/15)
An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developedviaa B(C6F5)3-catalyzed cycloaddition reaction ofo-(1-alkynyl)(thio)anisoles oro-(1-alkynyl)-N-methylaniline. In this reaction, benzenethiophene, benzofuran or indole skeletons could be constructed by an intermolecular cyclization with diphenylsilane. This protocol elicited moderate-to-good yields with metal-free reaction systems.
Copper-Catalyzed Annulation Cascades of Alkyne-Tethered α-Bromocarbonyls with Alkynes: An Access to Heteropolycycles
Liu, Bang,Yu, Jiang-Xi,Li, Yang,Li, Jin-Heng,He, De-Liang
supporting information, p. 2129 - 2132 (2018/04/30)
We here describe a new Cu-catalyzed annulation cascade of alkyne-tethered α-bromocarbonyls with common alkynes for the synthesis of various heteropolycycle frameworks, including 1H-benzo[de]quinolin-2(3H)-ones, 4H-dibenzo[de,g]quinolin-5(6H)-one, and benzo[de]chromen-2(3H)-one, which were constructed with high selectivity. This was achieved by two-component annulation cascades, rather than atom-transfer radical cyclization (ATRC), with alkyne-tethered α-bromocarbonyls for one-step accessing heteropolycycles via C-Br bond split, intramolecular cyclization, intermolecular [4 + 2] annulation, and aryl C(sp2)-H functionalization cascades.
Synthesis of carbonylated heteroaromatic compounds: Via visible-light-driven intramolecular decarboxylative cyclization of o -alkynylated carboxylic acids
Gao, Fei,Wang, Jiu-Tao,Liu, Lin-Lin,Ma, Na,Yang, Chao,Gao, Yuan,Xia, Wujiong
supporting information, p. 8533 - 8536 (2017/08/04)
An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids. This method is characterized by its b
Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides
Senadi, Gopal Chandru,Wang, Ji-Qi,Gore, Babasaheb Sopan,Wang, Jeh-Jeng
supporting information, p. 2747 - 2753 (2017/08/23)
An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo
Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides
Le, Christine M.,Sperger, Theresa,Fu, Rui,Hou, Xiao,Lim, Yong Hwan,Schoenebeck, Franziska,Lautens, Mark
supporting information, p. 14441 - 14448 (2016/11/13)
We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. Calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.
Modular Access to Tetrasubstituted Imidazolium Salts through Acid-Catalyzed Addition of Isocyanides to Propargylamines
Ghashghaei, Ouldouz,Revés, Marc,Kielland, Nicola,Lavilla, Rodolfo
supporting information, p. 4383 - 4388 (2015/07/27)
Propargylamines, prepared through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. The key step of the mechanism involves the generation of an amidine intermediate, from the isocyanide insertion into the N-H bond of the propargylamine, which in situ evolves by cyclization upon the alkyne moiety. The scope of the process is analyzed and only shows restrictions for aliphatic amines, whereas it is quite general regarding the aldehyde, alkyne and isocyanide inputs. The protocol allows the preparation of a wide array of adducts, tandem one-pot processes being also feasible. Mechanistic studies using selected substrates have been used to determine the profile of the reaction and some substitution and functional group limitations. Some post-synthetic transformations of the imidazolium salts have been performed as well. Propargylamines, synthesized through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. Tandem one-pot protocols allow direct access to these adducts from the commercially available inputs.
Direct construction of fused indoles by gold-catalyzed cascade cyclization of conjugated diynes
Naoe, Saori,Saito, Tatsuo,Uchiyama, Masanobu,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
supporting information, p. 1774 - 1777 (2015/04/14)
A gold-catalyzed cascade cyclization of aniline derivatives bearing a conjugated diyne moiety was developed. Following the 5-endo-dig indole formation, subsequent 7-endo-dig cyclization predominated over 6-exo-dig cyclization to give the indole fused with a seven-membered ring in good yields.
