6619-24-5Relevant academic research and scientific papers
Pd/C-catalyzed alkylation of heterocyclic nucleophiles with alcohols through the "borrowing hydrogen" process
Putra, Anggi Eka,Oe, Yohei,Ohta, Tetsuo
, p. 7799 - 7805 (2015/12/31)
The alkylation of heterocyclic compounds is important for the synthesis of various biologically active compounds. In this paper, we present the development of a Pd/C-catalyzed alkylation of heterocyclic compounds using alcohols as the alkylating agents. T
Efficient C-3 reductive alkylation of 4-hydroxycoumarin by dehydrogenative oxidation of benzylic alcohols through ruthenium catalysis
Montagut-Romans,Boulven,Lemaire,Popowycz
, p. 1794 - 1801 (2014/05/06)
A practical route to prepare 4-hydroxycoumarin derivatives functionalized at the C-3 position is described through a catalytic coupling reaction between 4-hydroxycoumarin and a series of substituted benzylic alcohols. The reaction is conducted in the pres
Multimetallic Ir-Sn3-catalyzed substitution reaction of π-activated alcohols with carbon and heteroatom nucleophiles
Maity, Arnab Kumar,Chatterjee, Paresh Nath,Roy, Sujit
, p. 942 - 956 (2013/07/25)
An atom economic and catalytic substitution reaction of π-activated alcohols by a multimetallic IreSn3 complex has been demonstrated. The multimetallic IreSn3 complex can be easily synthesized from the reaction between [Cp*IrCl2]2 and SnCl2. In presence of as little as 1 mol % of the catalyst three different types of π-activated alcohols, namely benzyl, allyl, and propargyl alcohols, have been successfully transformed into alkylated products using carbon (arenes, heteroarenes, allyltrimethylsilane, and 1,3-dicarbonyls), nitrogen (sulfonamides), oxygen (alcohols), and sulfur (thiols) nucleophiles in very high yields. An electrophilic mechanism is proposed from the Hammett correlation study.
The rhodium carbenoid route to 3-aryl-4-hydroxycoumarins: Synthesis of derrusnin
Goldoni, Luca,Cravotto, Giancarlo,Penoni, Andrea,Tollari, Stefano,Palmisano, Giovanni
, p. 927 - 930 (2007/10/03)
3-Aryl-4-hydroxycoumarins have been obtained in satisfactory yields and selectivity through a Rh(II)-mediated arylation of diazocoumarin. The utility of this approach is demonstrated by synthesis of the natural product derrusnin.
The Chemistry of Coumarin Derivatives Synthesis of 3-Alkyl-4-hydroxycoumarins by Reductive Fragmentation of 3,3'-Alkylidene-4,4'-dihydroxybis
Appendino, Giovanni,Cravotto, Giancarlo,Tagliapietra, Silvia,Ferraro, Stefano,Nano, Gian Mario,Palmisano, Giovanni
, p. 1451 - 1458 (2007/10/02)
Treatment of 3,3'-alkylidene-4,4'-dihydroxybis 1 with NaBH3CN in refluxing MeOH affords 3-alkyl-4-hydroxycoumarins 2 and 4-hydroxycoumarin (3; Scheme 1).The reaction may take place via hydride trapping of alkylidenechromandiones C formed from 1 in a retro-Michael reaction.Such a retro-Michael reaction of 1 might be biologically relevant.The presence of C during the reductive fragmentation 1 --> 2 is suggested by Diels-Alder and nucleophilic trapping of the alkylidenechromandiones C as well as from cross-over experiments with coumarins other than 3 (see Scheme 2).The reductive fragmentation of 1 allows the chemo- and regioselective synthesis of a variety of 3-alkyl-4-hydroxycoumarins 2 (see Table).
