73830-10-1Relevant academic research and scientific papers
Ru(ii)-catalyzed allenylation and sequential annulation of: N -tosylbenzamides with propargyl alcohols
Kumar, Shreemoyee,Nair, Akshay M.,Volla, Chandra M. R.
supporting information, p. 6280 - 6283 (2021/07/02)
We hereby report Ru(ii)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality of the afforded allenes allowed further transformations to expand the practicality of the protocol. This journal is
Neighboring Carbonyl Group Assisted Hydration of Unsymmetrical Aryl Alkynes Overriding Regular Selectivity
Mendhekar, Kishor L.,Pradhan, Tapas R.,Mallampudi, N. Arjunreddy,Mohapatra, Debendra K.
, p. 5787 - 5797 (2019/08/21)
A mild and highly regioselective gold-catalyzed hydration of γ-acetoxy aryl alkynes leading to anti-Markovnikov products by the assistance of a neighboring carbonyl group is presented. The reaction procedure operates under room temperature conditions with
Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids
Orha, László,Tukacs, József M.,Kollár, László,Mika, László T.
supporting information, p. 2907 - 2913 (2019/12/14)
It was demonstrated that the γ-valerolactone-based ionic liquid, tetrabutylphosphonium 4-ethoxyvalerate as a partially bio-based solvent can be utilized as alternative reaction medium for copper- and auxiliary base-free Pd-catalyzed Sonogashira coupling reactions of aryl iodides and functionalized acetylenes under mild conditions. Twenty-two cross-coupling products were isolated with good to excellent yields (72–99%) and purity (>98%). These results represent an example which proves that biomass-derived safer solvents can be utilized efficiently in common, industrially important transformations exhibiting higher chemical and environmental efficiency.
DBU-promoted carbonylative synthesis of 1,3-oxathiolan-2-ones from propargylic alcohols with TFBen as the CO source
Ying, Jun,Zhou, Chao,Wu, Xiao-Feng
supporting information, p. 1065 - 1067 (2018/02/22)
A DBU-promoted carbonylative cyclization of propargylic alcohols with sulfur was developed. Various 1,3-oxathiolan-2-ones were produced in 61-98% yields under mild conditions in the absence of metal catalysts. TFBen (benzene-1,3,5-triyl triformate) as an efficient and solid CO surrogate and S8 as an ideal sulfur source were employed and incorporated.
Tert-butoxy rare earth/sodium impurity bimetallic complex, as well as preparation method and use thereof
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Paragraph 0062-0063, (2017/07/13)
The invention discloses a tert-butoxy rare earth/sodium hetero-bimetallic complex as well as a preparation method and use thereof. The molecular formula of the tert-butoxy rare earth/sodium hetero-bimetallic complex is LnNa8[OC(CH3)3]10(OH), and Ln repres
Asymmetric Intermolecular Heck Reaction of Propargylic Acetates and Cycloalkenes to Access Fused Cyclobutenes
Jiao, Zhiwei,Shi, Qi,Zhou, Jianrong Steve
supporting information, p. 14567 - 14571 (2017/10/23)
An asymmetric Heck annulation of propargylic acetates with several types of cyclic olefins affords highly strained cyclobutenes in high enantioselectivity.
Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study
Tejedor, David,Cotos, Leandro,Márquez-Arce, Daniel,Odriozola-Gimeno, Mikel,Torrent-Sucarrat, Miquel,Cossío, Fernando P.,García-Tellado, Fernando
supporting information, p. 18280 - 18289 (2015/12/24)
The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6π electrocyclization, and an aromatization reaction.
Efficient catalytic transition-metal-free conditions for nucleophilic addition of arylacetylenes to aromatic ketones
Liu, Junfeng,Lin, Jin,Song, Ling
supporting information; experimental part, p. 2160 - 2163 (2012/05/05)
A mild, efficient, and transition-metal-free method for nucleophilic addition of arylacetylenes to diverse aromatic ketones, using catalytic amount of tetrabutylammonium chloride as a promoter and solid KOH as a base in THF, was developed to afford aromat
Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions
Ting, Chun-Ming,Hsu, Yi-Ling,Liu, Rai-Shung
supporting information; experimental part, p. 6577 - 6579 (2012/07/31)
We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.
Gold(l)-catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermodular addition of water and alcohols to epoxy alkynes
Dai, Lun-Zhi,Qi, Ming-Juan,Shi, Yong-Ling,Liu, Xu-Guang,Shi, Min
, p. 3191 - 3194 (2008/02/11)
We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by goid(l). This procedure involves a domino three-membered ring-opening, 6-exo-
