22800-73-3Relevant academic research and scientific papers
Palladium-Catalyzed Alkoxycarbonylation of sec-Benzylic Ethers
Beller, Matthias,Jackstell, Ralf,Maes, Bert U. W.,Schneider, Carolin
supporting information, (2020/02/25)
Herein, we report the palladium-catalyzed synthesis of 3-arylpropionate esters starting from secondary benzylic ethers. With this investigation it could be shown that ethers are suitable starting materials in addition to the established carbonylation reactions of olefins, alcohols, or aryl halides.
Site-Selective Alkoxylation of Benzylic C?H Bonds by Photoredox Catalysis
Lee, Byung Joo,DeGlopper, Kimberly S.,Yoon, Tehshik P.
supporting information, p. 197 - 202 (2019/11/26)
Methods that enable the direct C?H alkoxylation of complex organic molecules are significantly underdeveloped, particularly in comparison to analogous strategies for C?N and C?C bond formation. In particular, almost all methods for the incorporation of alcohols by C?H oxidation require the use of the alcohol component as a solvent or co-solvent. This condition limits the practical scope of these reactions to simple, inexpensive alcohols. Reported here is a photocatalytic protocol for the functionalization of benzylic C?H bonds with a wide range of oxygen nucleophiles. This strategy merges the photoredox activation of arenes with copper(II)-mediated oxidation of the resulting benzylic radicals, which enables the introduction of benzylic C?O bonds with high site selectivity, chemoselectivity, and functional-group tolerance using only two equivalents of the alcohol coupling partner. This method enables the late-stage introduction of complex alkoxy groups into bioactive molecules, providing a practical new tool with potential applications in synthesis and medicinal chemistry.
ANOMALOUS REDUCTION OF ALIPHATIC-AROMATIC KETONES BY THE COMPLEX HYDRIDES OF BORON
Dem'yanovich, V.M.,Khlebnikov, V.A.
, p. 255 - 259 (2007/10/02)
During the reduction of XC6H4COCH3 by the action of sodium borohydride or potassium borohydride in a water-methanol medium the ethers XC6H4CH(OCH3)CH3 and not the corresponding alcohols were obtained.The formation of the ethers indicates that the O-Calkyl (and not O-B) bond is broken in the intermediate tetraalkoxyborate if a stable carbocation of the benzylic type, further stabilized by an electron-donor group at the ortho or para position of the benzene ring, is formed.
Asymmetric synthesis of (R)-(+)-α-methyl-o-methoxybenzyl methyl ether via the stereoselective benzylic elaboration of tricarbonyl (η6-o-methoxybenzyl methyl ether)chromium(o)
Davies,Goodfellow,Sutton
, p. 1303 - 1316 (2007/10/02)
Treatment of tricarbonyl (η6-o-methoxybenzyl methyl ether)chromium(o) with t-butyllithium followed by an electrophile gives a single diastereoisomer of the corresponding alpha substituted complex. The relative configuration within the product f
