25724-96-3Relevant academic research and scientific papers
Copper-Catalyzed Oxidative Acetalization of Boronic Esters: An Umpolung Strategy for Cyclic Acetal Synthesis
Miller, Eric M.,Walczak, MacIej A.
, p. 8230 - 8239 (2020/07/15)
A protocol for the acetalization of boronic esters is described. The reaction is catalyzed by copper, and the conditions proved to be mild and were amenable to a variety of functional groups. We expanded the Chan-Lam coupling to include C(sp3) nucleophiles and converted them into corresponding acetals. This method allows for the orthogonal acetalization of substrates with reactive, acid-sensitive functional groups.
Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds
Yang, Chun-Hua,Fan, Huihui,Li, Huimin,Hou, Shenyin,Sun, Xiangkun,Luo, Donghao,Zhang, Yinchao,Yang, Zhantao,Chang, Junbiao
supporting information, p. 9438 - 9441 (2019/11/20)
A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.
Selectivity in Garratt-Braverman cyclization: An experimental and computational study
Maji, Manasi,Mallick, Dibyendu,Mondal, Sayantan,Anoop, Anakuthil,Bag, Subhendu Sekhar,Basak, Amit,Jemmis, Eluvathingal D.
supporting information; experimental part, p. 888 - 891 (2011/04/27)
Bispropargyl sulfones equipped with aromatic rings of dissimilar nature were synthesized. Under basic conditions, these sulfones isomerized to the bisallenic sulfones, creating a competitive scenario between two alternate Garratt-Braverman (GB) cyclizatio
Copper(I)-catalyzed Caryl-Calkynyl bond formation of aryl iodides with terminal alkynes
Thakur,Sekar
scheme or table, p. 2785 - 2789 (2010/01/21)
A wide range of internal alkynes are synthesized from the corresponding aryl iodides and terminal alkynes by Sonogashira-type cross-coupling reactions through Caryl-Calkynyl bond formation in the presence of a catalytic amount of readily available DBU-CuBr complex under mild reaction conditions. Georg Thieme Verlag Stuttgart.
An efficient copper(I) complex catalyzed Sonogashira type cross-coupling of aryl halides with terminal alkynes
Thakur,Jaseer,Naidu, Ajay B.,Sekar, Govindasamy
experimental part, p. 2865 - 2869 (2009/09/06)
A wide range of arylated alkynes are synthesized from the corresponding aryl halides and terminal alkynes through Sonogashira type cross-coupling reactions through C(aryl)-C bond formation in the presence of a catalytic amount of N,N′-dibenzyl BINAM-CuI complex under mild reaction conditions.
A copper-free Sonogashira reaction using a Pd/MgLa mixed oxide
Cwik, Agnieszka,Hell, Zoltán,Figueras, Fran?ois
, p. 3023 - 3026 (2007/10/03)
A new Pd/MgLa mixed oxide is found to be an efficient catalyst for the Sonogashira reaction of aryl iodides, bromides and even activated chlorides in the absence of a copper salt.
Pt(0)-catalyzed alkynylation of aryl iodides with lithium alkynyltriisopropoxy borates
Oh, Chang Ho,Reddy, V. Raghava
, p. 2091 - 2094 (2007/10/03)
An efficient cross coupling reaction of various lithium alkynyltriiospropoxyborates with a wide array of aryl iodides was catalyzed by Pt(PPh3)4-CuI in DMF as a solvent. These cross coupling reactions are general and permit the new sp-sp2 carbon-carbon bond formation.
Synthesis of Aryl- and Vinylacetylene Derivatives by Copper-Catalyzed Reaction of Aryl and Vinyl Iodides with Terminal Alkynes
Okuro, Kazumi,Furuune, Makoto,Enna, Masahiro,Miura, Masahiro,Nomura, Masakatsu
, p. 4716 - 4721 (2007/10/02)
The coupling reaction of aryl iodides with terminal alkynes by using a catalyst system of CuI-PPh3 in the presence of K2CO3 as base gives the corresponding arylated alkynes in excellent yields.Addition of PPh3 is essential for the reaction to proceed catalytically.Vinyl iodides also react smoothly with the alkynes to give enyne compounds with retention of the configurations.While DMF and DMSO can be used as solvents, DMSO is found to be effective for the reaction with aliphatic terminal alkynes.A reaction mechanism involving initial formation of copper acetylide species coordinated by PPh3 followed by reaction of aryl and vinyl iodides is proposed.
