16930-95-3Relevant articles and documents
Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3- azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes
Durham, Robin,Mandel, Jeremie,Blanchard, Nicolas,Tam, William
, p. 1494 - 1505 (2011)
Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3- azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes were investigated. Yields of up to 90% were obtained though regioselectivity was modest. Select cycloadducts could be separated and used to access a highly functionalized [3.2.0] bicyclic structure through reductive cleavage of the N-O bond. These ring-opened products displayed a chemical exchange phenomenon in 1D carbon NMR and required characterization by 2D NMR techniques.
Mild Palladium-catalysed Carbonylation of Alkynylphenyliodonium Toluene-p-sulphonates under Carbon Monoxide at Atmospheric Pressure
Kitamura, Tsugio,Mihara, Ichiro,Taniguchi, Hiroshi,Stang, Peter J.
, p. 614 - 615 (1990)
Alkoxycarbonylation of alkynylphenyliodonium toluene-p-sulphonates catalysed by a palladium catalyst proceeded under carbon monoxide at atmospheric pressure at room temperature to give alkyne carboxylates in high yields.
Phosphine-Catalyzed Intermolecular Dienylation of Alkynoate with para-Quinone Methides
Song, Zefeng,Wang, Weijia,Liu, Zhixin,Lu, Yue,Wang, De
supporting information, p. 8590 - 8599 (2021/07/20)
An interesting remote I-C 1,6-Addition and an isomerization cascade reaction for phosphine-catalyzed activated alkynes have been disclosed. The products featuring a functional diene and a 1,1-diaryl methyl motif have been obtained in moderate to good yields (30-86%) by applying para-quinone methides (p-QMs) and I-substituted alkynoate with tributylphosphine (PnBu3) catalysis, along with high regioselectivity and stereoselectivity (dr > 20:1). The wide scope of compatible substrates (35 examples), such as indolyl, oxindolyl, ester, and cinnamyl, expand the utility of this methodology. A plausible mechanism and some applications of it have also been presented.
Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides
Fernandes, Rodney A.,Gangani, Ashvin J.,Kunkalkar, Rupesh A.
, p. 3970 - 3984 (2020/03/19)
An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.
Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles
Sahani, Rajkumar Lalji,Liu, Rai-Shung
supporting information, p. 1026 - 1030 (2017/01/18)
Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.
Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives
Karad, Somnath Narayan,Chung, Wei-Kang,Liu, Rai-Shung
supporting information, p. 13004 - 13007 (2015/08/06)
Gold-catalyzed formal hetero-[4π+2π] cycloadditions of tert-butyl propiolates with carbonyl compounds proceeded efficiently to yield 4H-1,3-dioxine derivatives over a wide scope of substrates. With acetone as a promoter, gold-catalyzed cycloadditions of these propiolate derivatives with enol ethers led to the formation of atypical [4+2]-cycloadducts with skeletal rearrangement.
Catalysts for the alkyne metathesis
-
Page/Page column 27; 28; 40; 41, (2015/04/15)
Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.
Platinum-catalyzed hydrosilylations of internal alkynes: Harnessing substituent effects to achieve high regioselectivity
Rooke, Douglas A.,Ferreira, Eric M.
supporting information; experimental part, p. 3225 - 3230 (2012/05/31)
Rule of thumb: The high yielding title reaction is described with a focus on understanding the factors that govern the regioselectivity of the process (see scheme). Electronic, steric, and functional group properties all influence the selectivity, an understanding of which allows the selective formation of trisubstituted vinylsilanes, which are synthetically useful compounds for accessing stereodefined alkenes. Copyright
Rhodium-catalyzed aryl- and alkylation-oligomerization of alkynoates with organoboron reagents giving salicylates
Yasuhara, Yuichi,Nishimura, Takahiro,Hayashi, Tamio
supporting information; experimental part, p. 2130 - 2132 (2010/08/04)
The reaction of alkynoates with aryl- or alkylboron reagents in the presence of a rhodium/diene catalyst gave high yields of salicylate derivatives with high selectivity, which consist of three or four molecules of the alkynoate and one organic group derived from the organoboron reagents. The Royal Society of Chemistry.
Asymmetric conjugate silyl transfer in iterative catalytic sequences: Synthesis of the C7-C16 fragment of (+)-neopeltolide
Hartmann, Eduard,Oestreich, Martin
supporting information; experimental part, p. 6195 - 6198 (2010/11/17)
Matched or mismatched, that is not the question! The anti,anti configuration of the C7- C16 fragment of (+)-neopeltolide is stereoselectively installed in an iterative sequence of catalyst-controlled Si group and Me group transfers, even with mismatched selectivity in the former (Si=Me2PhSi, see scheme; TBS=tert-butyldimethylsilyl).
