27980-54-7Relevant academic research and scientific papers
Catalytic Amide-Base System of TMAF and N(TMS)3 for Deprotonative Coupling of Benzylic C(sp3)-H Bonds with Carbonyls
Shigeno, Masanori,Nakaji, Kunihito,Nozawa-Kumada, Kanako,Kondo, Yoshinori
, p. 2588 - 2592 (2019)
This paper describes that an amide-base generated in situ from tetramethylammonium fluoride (TMAF) and N(TMS)3 catalyzes the deprotonative coupling of benzylic C(sp3)-H bonds with carbonyls to form stilbenes. A variety of methylheteroarenes (2-methylbenzothiophene, 2-methylbenzofuran, and 2-, 3-, or 4-methylpyridines) are used as nucleophiles. Application to enamine synthesis using DMF as an electrophile is also shown. The present system is effective for toluenes (4-phenyl-, 4-bromo-, 2-bromo-, and 4-chlorotoluenes) having low reactivity.
Pd-Catalyzed Autotandem Reactions with N-Tosylhydrazones. Synthesis of Condensed Carbo- and Heterocycles by Formation of a C-C Single Bond and a C-C Double Bond on the Same Carbon Atom
Paraja, Miguel,Valdés, Carlos
, p. 2034 - 2037 (2017/04/27)
A new Pd-catalyzed autotandem reaction is introduced that consists of the cross-coupling of a benzyl bromide with a N-tosylhydrazone followed by an intramolecular Heck reaction with an aryl bromide. During the process, a single and a double C-C bond are formed on the same carbon atom. Two different arrangements for the reactive functional groups are possible, rendering great flexibility to the transformation. The same strategy led to 9-methylene-9H-fluorenes, 9-methylene-9H-xanthenes, 9-methylene-9,10-dihydroacridines, and also dihydropyrroloisoquinoline and dihydroindoloisoquinoline derivatives.
Organic Reactive Intermediates: Part XI - Preparation and Reactions of Xanthenyl Ylids
Handoo, Kishan L.,Kaul, Anju
, p. 1 - 2 (2007/10/02)
Two new xanthenyl ylids, viz. triphenylphosphoniumxanthen-9-ylid and triphenylphosphoniumthioxanthen-9-ylid have been prepared.The former undergoes normal Wittig reaction with a number of carbonyl compounds yielding olefins.
Studies on Betaine Decomposition of Arsonium Ylides
Tewari, R. S.,Suri, S. K.,Gupta, K. C.
, p. 95 - 98 (2007/10/02)
A systematic study on the nature of decomposition of betaine formed by nucleophilic attack of semistabilized arsonium ylides on thiocarbonyl substrates has been carried out.A series of substituted benzylidenetriphenylarsenanes have been generated from their corresponding salts and condensed with few cyclic thioketones to yield exocyclic olefins as exclusive products.The non-availability of thioepoxides indicates that the mode of decomposition of such type of betaines is quite analogous to the betaine formed by phosphonium ylides.The structure of the products have been assigned by IR and NMR spectral studies. - Keywords: Betaine, Arsonium Ylides
