857026-45-0Relevant articles and documents
Metal-Free Domino Oligocyclization Reactions of Enynals and Enynones with Molecular Oxygen
Abbasi Kejani, Alireza,Khosravi, Hormoz,Rominger, Frank,Balalaie, Saeed,Breit, Bernhard
supporting information, p. 1291 - 1295 (2021/02/20)
A novel metal-free direct addition of molecular oxygen to the C-C triple bond toward benzannulated oxygen-bridged seven-membered ring systems and aza[3.1.0]bicycle skeletons under 3O2 atmosphere has been described. The reaction proceeds through at least three intramolecular C-O and C-C bond forming steps via green, simple, and unprecedented domino radical processes with high selectivity and good yields.
Synthesis of N-(isoquinolin-1-yl)sulfonamides via Ag2O-catalyzed tandem reaction of ortho-alkynylbenzaldoximes with benchtop stabilized ketenimines
Hayatgheybi, Sepideh,Khosravi, Hormoz,Zahedian Tejeneki, Hossein,Rominger, Frank,Bijanzadeh, Hamid Reza,Balalaie, Saeed
supporting information, p. 3524 - 3529 (2021/05/10)
In this project, a moderately efficient approach to multisubstituted N-(isoquinolin-1-yl)sulfonamide derivatives was illustrated, utilizing ortho-alkynylbenzaldoximes and zwitterionic ketenimine salts in a tandem reaction catalyzed by silver oxide. The oxophilicity of Ag2O, along with its nature as Lewis acid, pave the way for a smooth [3 + 2] cycloaddition between isoquinoline N-oxides and ketenimine species, which is a key step in this reaction. DFT calculation suggests that 1,3-dipolar cycloaddition of nitrone and ketenimine proceeds through a selective stepwise mechanism.
Iodine promoted cascade cycloisomerization of 1-en-6,11-diynes
Qiu, Yi-Feng,Niu, Yue-Jie,Song, Xian-Rong,Wei, Xi,Chen, Hui,Li, Shun-Xi,Wang, Xi-Cun,Huo, Congde,Quan, Zheng-Jun,Liang, Yong-Min
supporting information, p. 1421 - 1424 (2020/02/11)
An iodine promoted cascade cycloisomerization of 1-en-6,11-diynes is presented for the easy preparation of tetrahydrobenzo[f]isoquinolines. This developed reaction system is identified as having good functional-group applicability and can be scaled up to gram quantities. In this transformation, two new cyclic frameworks and one carbonyl group are formed with four new bonds constructed. Additionally, the resulting iodo-substituted compounds could be further derived through simple elimination reactions.
Gold-catalyzed synthesis of 1-naphthylcarbenoids and their synthetic utilization in cyclopropanation reactions
Lauterbach, Tobias,Ganschow, Michael,Hussong, Matthias W.,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 680 - 686 (2014/04/03)
1-Naphthylcarbenoids are generated via 1,2-acyl migration and subsequent carbene shift from simple, easily available diyne starting materials. These highly reactive species were allowed to react with differently substituted alkenes in both intermolecular and intramolecular fashions. In the intermolecular cases even a simple 1:1 ratio of the starting materials delivered the corresponding cyclopropylnaphthalenes in high yields by the use of a gold(III) catalyst. The methodology offers a completely new approach to these valuable targets, the new route represents an efficient alternative to common methods that are based on cross-coupling strategies.
Gold-catalyzed cascade reaction of hydroxy enynes for the synthesis of oxanorbornenes and naphthalene derivatives
Song, Xian-Rong,Xia, Xiao-Feng,Song, Qing-Bao,Yang, Fang,Li, Ying-Xiu,Liu, Xue-Yuan,Liang, Yong-Min
supporting information; experimental part, p. 3344 - 3347 (2012/09/08)
An efficient and selective gold-catalyzed cascade reaction for the synthesis of oxanorbornenes and naphthalene derivatives from easily prepared hydroxy enynes has been developed. Divergent products could be obtained from the same substrates by different g
Gold-catalyzed waste-free generation and reaction of azomethine ylides: Internal redox/dipolar cycloaddition cascade
Yeom, Hyun-Suk,Lee, Ji-Eun,Shin, Seunghoon
supporting information; experimental part, p. 7040 - 7043 (2009/04/07)
(Chemical Equation Presented) High-octane synthesis: Azomethine ylides can be generated from an internal redox reaction of a nitrone-tethered alkyne under electrophilic metal catalysis (see scheme; M=metal). This novel and atom-economical generation of an azomethine ylide does not involve potentially explosive diazo derivatives. The azomethine ylide can participate in a dipolar cycloaddition cascade to provide an azabicyclo[3.2.1]octane.