منابع مشابه
Palladium-Catalyzed Allylation/Benzylation of H-Phosphinate Esters with Alcohols.
The Pd-catalyzed direct alkylation of H-phosphinic acids and hypophosphorous acid with allylic/benzylic alcohols has been described previously. Here, the extension of this methodology to H-phosphinate esters is presented. The new reaction appears general, although its scope is narrower than with the acids, and its mechanism is likely different. Various alcohols are examined in their reaction wi...
متن کاملRetro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles.
A new strategy has been developed for the benzylation of nitriles directly from benzyl alcohols. In this process benzyl alcohols undergo retro-Claisen activation with cyanoacetic esters to generate an active electrophile and a carbanionic nucleophile. In the presence of Pd(0) these intermediates undergo catalytic coupling to generate a new C-C bond, resulting in the formation of phenyl propioni...
متن کاملHot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols.
In refluxing 9 : 1 (v/v) H2O-1,4-dioxane and without an additional catalyst, the rearrangements of various types of cyclopropyl carbinols were attempted. It was found that the reactions generally gave homoallylic alcohols in good to very high chemical yields. Rearrangements of bicyclic or tricyclic cyclopropyl carbinols readily gave the desired ring-expanded cyclic homoallylic alcohols which ar...
متن کاملPalladium-catalyzed S-benzylation of unprotected mercaptobenzoic acid with benzyl alcohols in water.
Palladium-catalyzed S-benzylation of unprotected mercaptobenzoic acids with benzyl alcohols gave only S-benzylated mercaptobenzoic acids in good yields. Water may play an important role for the smooth generation of the (η(3)-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.
متن کاملSpin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols.
Nature routinely engages alcohols as leaving groups, as DNA biosynthesis relies on the removal of water from ribonucleoside diphosphates by a radical-mediated "spin-center shift" (SCS) mechanism. Alcohols, however, remain underused as alkylating agents in synthetic chemistry due to their low reactivity in two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes usi...
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ژورنال
عنوان ژورنال: Bulletin of the Chemical Society of Japan
سال: 1986
ISSN: 0009-2673,1348-0634
DOI: 10.1246/bcsj.59.1761