An oxidative methyl esterification of aldehydes was effectively achieved. The trivalent indium reagent, indium(III) triflate, was revealed to accelerate the reactions in many cases. Aromatic aldehydes with various substituents were subjected to this method, and each produced the corresponding methyl esters in good to excellent yields within a relatively short reaction time.
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http://dx.doi.org/10.1248/cpb.c13-00072 | DOI Listing |
J Am Chem Soc
April 2020
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel.
Oxidation by water with H liberation is highly desirable, as it can serve as an environmentally friendly way for the oxidation of organic compounds. Herein, we report the oxidation of alkenes with water as the oxidant by using a catalyst combination of a dearomatized acridine-based PNP-Ru complex and indium(III) triflate. Compared to traditional Wacker-type oxidation, this transformation avoids the use of added chemical oxidants and liberates hydrogen gas as the only byproduct.
View Article and Find Full Text PDFJ Org Chem
November 2019
Department of Chemistry , Dalhousie University, P.O. Box 15000 Halifax , Nova Scotia B3H 4R2 , Canada.
The cyclization of a series of nonheterocyclic allenyl aryl ketones was examined using boron trifluoride etherate and indium triflate to mediate the reaction. Yields with BF were low in most instances due mainly to competitive destruction of the substrates. With In(OTf), there was less decomposition, and the yields of the cyclized product were much higher, but only for substrates with electron-donating substituents.
View Article and Find Full Text PDFJ Org Chem
April 2018
Department of Chemistry , National Institute of Technology, Tiruchirappalli - 620 015 , Tamil Nadu , India.
The indium(III) triflate-catalyzed reaction of aza-Michael adducts of chalcones with aromatic amines has been investigated. The Michael adducts derived from substituted anilines and chalcones underwent retro-Michael addition to give the original starting materials, whereas the adducts derived from 1-naphthylamines and chalcones afforded quinolines. A six-membered cyclic transition state has been proposed to explain the retro-Michael addition, while a Povarov mechanism has been put forward to explain the quinoline formation.
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
August 2017
Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare.
The efficient oxidation of benzylic alcohols to carbonyl compounds was performed using chloramine-T and a catalytic amount of indium(III) triflate. The primary benzylic alcohols were converted to the corresponding aldehydes in a good yield, and the secondary benzylic alcohols were oxidized to ketones in a high yield. The optimized reaction conditions required 0.
View Article and Find Full Text PDFJ Org Chem
March 2016
Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, United States.
Nucleoside O-glycosylation represents an archetypal problem in chemical selectivity, inasmuch as the nucleobase (an undesired site of reaction) is usually more nucleophilic than the hydroxyl (the desired site of reaction). Optimized reaction conditions have been developed for the efficient O-glycosylation of nucleoside hydroxyls. Both thioglycoside and Schmidt imidate donors (1.
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