681427-53-2Relevant academic research and scientific papers
Au(I)-Catalyzed 6-endo-dig Cyclizations of Aromatic 1,5-Enynes to 2-(Naphthalen-2-yl)anilines Leading to Divergent Syntheses of Benzo[α]carbazole, Benzo[c,h]cinnoline and Dibenzo[i]phenanthridine Derivatives
Fu, Jiayue,Li, Bingbing,Wang, Xiugui,Liang, Qida,Peng, Xiaoshi,Yang, Lu,Wan, Tao,Wang, Xinxiu,Lin, Bin,Cheng, Maosheng,Liu, Yongxiang
supporting information, p. 46 - 52 (2021/11/20)
A gold(I)-catalyzed 6-endo-dig cyclization of aromatic 1,5-enynes was developed to synthesize 2-(naphthalen-2-yl)anilines. The functional group tolerance of this cyclization was examined systematically and a possible mechanism was proposed. The derivatization of 2-(naphthalen-2-yl)aniline was carried out to facile access to benzo[α]carbazole, benzo[c,h]cinnoline and dibenzo[i]phenanthridine derivatives in a divergent way.
Catalytic Cyclotrimerization Pathway for Synthesis of Selaginpulvilins C and D: Scope and Limitations
Rycek, Lukas,Mateus, Miguel,Beytlerová, Nela,Kotora, Martin
, p. 4511 - 4515 (2021/04/12)
A facile and unified approach to the main selaginpulvilin's framework was achieved by catalytic [2 + 2 + 2]-cyclotrimerization of a triyne with monosubtituted alkynes. The reaction proceeded with high "ortho"selectivity by using Wilkinson's catalyst (RhCl
Synthesis of phthalan derivatives via a formal intramolecular 1,3-insertion of rhodium(II) azavinyl carbenes into O[sbnd]Si bond
Deng, Changchang,Duan, Shengguo,Jie, Yuchen,Luo, Huan,Xiang, Qiaoyi,Xu, Ze-Feng
supporting information, (2021/08/30)
The first formal intramolecular 1,3-insertion into O[sbnd]Si bond of rhodium(II) azavinyl carbene have been developed, and valuable phthalan derivatives could be synthesized efficiently. In addition, various functional groups could be introduced to the pr
Photocatalytic Decarboxylative [3 + 2] and [4 + 2] Annulation of Enynals and γ,σ-Unsaturated N-(Acyloxy)phthalimides by NaI/PPh3Catalysis
Liu, Xiao-Jie,Zhou, Sheng-Yun,Xiao, Yuting,Sun, Qing,Lu, Xin,Li, Yang,Li, Jin-Heng
supporting information, p. 7839 - 7844 (2021/10/20)
A practical and eco-friendly strategy for the radical-mediated decarboxylative [3 + 2] and [4 + 2] annulation of enynals and γ,σ-unsaturated N-(acyloxy)phthalimides through the photoactivation of an electron donor-acceptor (EDA) complex has been developed. A wide range of primary, secondary, and tertiary alkyl N-hydroxyphthalimide (NHP) esters can be used as suitable substrates for the synthesis of fused ketones without any transition-metal catalysts or oxidants. This protocol features a broad substrate scope, excellent selectivity, and clean reaction conditions.
A Gold(I)-Catalyzed Tandem Cyclization to Benzo[b]indeno[1,2-e][1,4]diazepines from o-Phenylenediamines and Ynones
Xie, Fukai,Zhang, Bo,Chen, Yanyu,Jia, Hongwei,Sun, Lei,Zhuang, Kaitong,Yin, Lili,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
supporting information, p. 3886 - 3897 (2020/08/06)
A gold-catalyzed tandem cyclization of o-phenylenediamines with ynones to synthesize benzo[b]indeno[1,2-e][1,4]diazepine has been developed. The mechanism was explored by control experiments. The method provides a way to access a range of benzo[b]indeno[1,2-e][1,4]diazepine derivatives in diversity-oriented synthesis aiming at discovering structurally diverse scaffolds. (Figure presented.).
Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes
Yu, Bangkui,Yu, Houjian,Huang, Hanmin
, p. 8962 - 8966 (2020/11/13)
A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.
Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles
Hong, Feng-Lin,Wang, Ze-Shu,Wei, Dong-Dong,Zhai, Tong-Yi,Deng, Guo-Cheng,Lu, Xin,Liu, Rai-Shung,Ye, Long-Wu
supporting information, p. 16961 - 16970 (2019/10/16)
The generation of metal carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. However, most of these transformations are based on the use of noble-metal catalysts and successful examples of such an asymmetric version are still very scarce. Here a copper-catalyzed enantioselective cascade cyclization of N-propargyl ynamides is reported, enabling the practical and atom-economical construction of diverse chiral polycyclic pyrroles in generally good to excellent yields with wide substrate scope and excellent enantioselectivities (up to 97:3 e.r.). Importantly, this protocol represents the first copper-catalyzed asymmetric diyne cyclization. Moreover, mechanistic studies revealed that the generation of donor/donor copper carbenes is presumably involved in this 1,5-diyne cyclization, which is distinctively different from the related gold catalysis, and thus it constitutes a novel way for the generation of donor/donor metal carbenes.
Synthesis of Fluorescent Azafluorenones and Derivatives via a Ruthenium-Catalyzed [2 + 2 + 2] Cycloaddition
Ye, Fei,Tran, Christine,Jullien, Ludovic,Le Saux, Thomas,Haddad, Mansour,Michelet, Véronique,Ratovelomanana-Vidal, Virginie
supporting information, p. 4950 - 4953 (2018/08/24)
An original and mild synthetic route for the preparation of novel azafluorenones and derivatives via a ruthenium-mediated [2 + 2 + 2] cycloaddition of α,ω-diynes and cyanamides has been developed. This atom-economical catalytic process demonstrated remarkable regioselectivities to access fluorescent azafluorenone derivatives. The photophysical properties of azafluorenone derivatives have been evaluated, and photoluminescence phenomena at solid and liquid states have been highlighted.
Syntheses of 12H-benzo[a]xanthen-12-ones and benzo[a]acridin-12(7H)-ones through Au(i)-catalyzed Michael addition/6-endo-trig cyclization/aromatization cascade annulation
Xiong, Zhiling,Zhang, Xinhang,Li, Yangming,Peng, Xiaoshi,Fu, Jiayue,Guo, Jiajia,Xie, Fukai,Jiang, Chongguo,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
, p. 7361 - 7374 (2018/10/24)
A multifaceted gold(i)-catalyzed aromaticity-driven double 6-endo cascade cyclization strategy to synthesize both 12H-benzo[a]xanthen-12-ones and benzo[a]acridin-12(7H)-ones, whose core motifs xanthone and acridone both exist as important scaffolds in an
De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes
Rong, Ming-Guang,Qin, Tian-Zhu,Liu, Xin-Rui,Wang, Hong-Fa,Zi, Weiwei
supporting information, p. 6289 - 6293 (2018/10/09)
In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.
