15311-10-1Relevant academic research and scientific papers
Carboxyboronate: A Versatile C1 Building Block
Holownia, Aleksandra,Tien, Chieh-Hung,Diaz, Diego B.,Larson, Reed T.,Yudin, Andrei K.
supporting information, p. 15148 - 15153 (2019/11/05)
The synthesis and applications of carboxy-MIDA-boronate, a novel C1 building block, are described. This molecule is accessible via a ruthenium tetraoxide-mediated cleavage of commercially available ethynyl-MIDA-boronate. In the course of this study, carboxy-MIDA-boronate was found to possess ambident reactivity towards nucleophiles. Carboxylic acid derivatization produces a broad range of previously unknown carbamoyl-, oxycarbo- and thiocarboboronates. Carboxy-MIDA-boronate and its derivatives undergo condensations to access borylated heterocycles with boron at positions that are difficult to access using alternate methods. The resulting heterocycles participate in the Suzuki–Miyaura cross-coupling reaction, enabling entry into diverse bis(heteroaryl) motifs. The carbon monoxide-releasing capacity of carboxy-MIDA-boronate was also examined and applied in palladium-catalyzed carbonylation.
Pd/Cu-catalyzed C-H arylation of 1,3,4-thiadiazoles with (hetero)aryl iodides, bromides, and triflates
Vachhani, Dipak D.,Sharma, Abhishek,Van Der Eycken, Erik
, p. 8768 - 8774 (2012/11/07)
The direct C-H arylation of 1,3,4-thiadiazoles with a wide range of (hetero)aryl iodides, bromides, and triflates is described using a Pd/Cu-catalyzed protocol. The methodology is compatible with substrates possessing electron-donating or electron-withdrawing substituents and also tolerates sterically hindered aryl halides. The utility of the developed protocol is demonstrated by a one-pot C-H arylation-Suzuki coupling sequence.
HETEROCYCLIZATION OF DERIVATIVES OF THIONCARBOXYLIC ACIDS TO 1,3,4-THIADIAZOLES UNDER THE ACTION OF TERT-BUTYL HYPOCHLORITE
Demchuk, D. V.,Lutsenko, A. I.,Troyanskii, E. I.,Nikishin, G. I.
, p. 1690 - 1695 (2007/10/02)
A method for synthesis of 2-alkyl-5-aryl- and 2,5-diaryl-1,3,4-thiadiazoles by successive reaction of thioamides with tert-butyl hypochlorite and benzothiohydrazides was developed.The first step in the formation of 1,3,4-thiadiazoles consists of oxidation
Thiadiazoles and Thiadiazolines. Part 3. Synthesis of Triazol-3-yl-Δ2-1,3,4-thiadiazolines and a New Synthesis of Unsymmetrical 2,5-Di-substituted 1,3,4-Thiadiazoles
Moss, Stephen F.,Taylor, David R.
, p. 1987 - 1992 (2007/10/02)
The reaction of 1-chloro-1,4-diphenyl-2,3-diazabutadiene (1) with 1-acetyl- and with 1-benzoyl-thiosemicarbazide yields initially the hydrochlorides of N2-acetyl- and N2-benzoyl-Δ2-1,3,4-thiadiazoline-4-carboxamide hydrazo
