196952-95-1Relevant academic research and scientific papers
Revisiting the Addition of in-situ Nucleophiles to Allenic Ketones: An Entry Towards Synthesis of Benzodioxins
Sahoo, Sushree Ranjan,Sarkar, Debayan
supporting information, p. 1727 - 1731 (2020/03/13)
The manuscript delineates a revisit towards regioselective addition of in situ generated negative nucleophiles to allenic ketones in the presence of a base. A wide variety of allenic ketones as well as nucleophiles are viable in this transformation. A dir
Synthesis of Acyl Alkenylindium Reagents and Their Application in the Synthesis of (Z)-α,β-Unsaturated Ketones via Palladium-Catalyzed Cross-Coupling Reaction
Park, Youngchul,Min, Jiae,Eom, Dahan,Lee, Phil Ho
supporting information, p. 3934 - 3937 (2015/08/19)
A synthetic method for the preparation of acyl alkenylindium reagents was developed involving the hydroindation reaction of allenyl ketones with indium and indium chloride in methanol under mild conditions. Their synthetic applications were demonstrated from Pd-catalyzed cross-coupling reactions with aryl bromides and iodides and alkenyl and aryl triflates for the synthesis of (Z)-α,β-unsaturated ketones.
Synthesis of 1,2-allenic ketones through oxidation of homopropargyl alcohols with CrO3(cat.)/TBHP under MWI
Zhang, Xin Ying,Qu, Ying Ying,Wang, Yang Yang,Fan, Xue Sen
experimental part, p. 268 - 271 (2012/01/30)
A CrO3 catalyzed oxidation of homopropargyl alcohols with tert-butyl hydroperoxide under microwave irradiation was found to be an efficient and rapid alternative for the preparation of 1,2-allenic ketones. The advantages of this procedure inclu
Tandem reactions of 1,2-allenic ketones leading to substituted benzenes and α,β-unsaturated nitriles
Zhang, Xinying,Jia, Xuefei,Fang, Liangliang,Liu, Nan,Wang, Jianji,Fan, Xuesen
supporting information; experimental part, p. 5024 - 5027 (2011/11/12)
One-pot double Michael addition/intramolecular aldol reaction/ decarboxylation of 1,2-allenic ketones with cyanoacetate offers an efficient and convenient approach to highly functionalized benzenes. With 2-substituted cyanoacetates, the reaction proceeds via a different tandem process to afford α,β-unsaturated nitriles effectively.
Ru(III)-catalyzed oxidation of homopropargyl alcohols in ionic liquid: an efficient and green route to 1,2-allenic ketones
Fan, Xuesen,Qu, Yingying,Wang, Yangyang,Zhang, Xinying,Wang, Jianji
scheme or table, p. 2123 - 2126 (2010/06/14)
An efficient and environmentally benign synthesis of 1,2-allenic ketones via RuCl3-catalyzed oxidation of homopropargyl alcohols in ionic liquid with tert-butyl hydroperoxide (TBHP) as the oxidant was reported for the first time. With its reasonable efficiency and green nature, this oxidation provides a novel alternative route to 1,2-allenic ketones.
Indium-mediated highly regioselective reaction of prop-2-ynyl bromides with acyl cyanides in aqueous media: A convenient synthesis of allenic and propargylic ketones
Yoo, Byung-Woo,Lee, Sung-Jae,Choi, Kwang-Hyun,Keum, Sam-Rok,Ko, Jae-Jung,Choi, Kyung-Il,Kim, Joong-Hyup
, p. 7287 - 7289 (2007/10/03)
Indium-mediated reaction of acyl cyanides 1 with prop-2-ynyl bromides 2 in aqueous media occurs regioselectively to afford either allenic 3 or propargylic ketones 4 depending on the γ-substituent of the prop-2-ynyl bromide under the mild conditions.
C-C-Bond Formation by the Palladium-Catalyzed Cycloisomerization/Dimerization of Terminal Allenyl Ketones: Selectivity and Mechanistic Aspects
Hashmi, A. Stephen K.,Ruppert, Thorsten L.,Knoefel, Thomas,Bats, Jan W.
, p. 7295 - 7304 (2007/10/03)
The scope of the palladium-catalyzed cyclization/dimerization of terminal allenyl ketones 1 to the 2,4-disubstituted furans 3 has been investigated. Simplified and improved conditions almost exclusively provided the dimer 3, accompanied by only traces of the easily separable monomer 2. The formation of an isomer of 3, the unconjugated ketone 4, was completeley suppressed. Under these mild conditions, besides the normal functional group tolerance known for palladium-catalyzed reactions, an interesting selectivity was observed with functional groups that are known to react either in palladium-catalyzed reactions or reactions catalyzed by other transition-metals. Thus aryl halides, terminal alkynes, 1,6-enynes, and α-allenic alcohols were tolerated. In the latter example the selective reaction of only one out of two different allenes was achieved. Mechanistic investigation indicated a Pd(II)/Pd(IV)-cycle involving palladium(II)-γ-alkoxyvinylcarbene and furylpalladium(IV) hydride intermediates, although a second pathway for the formation of the dimer 3 which also involves Pd(IV)-intermediates like the 3,4-dimethylenepalladacyclopentane 23 and the 3-methylenepalladacyclobutane-like structure 15 (respectively 25) could not completely be excluded.
