Literature DB >> 17217292

Surfactant-type Brønsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water.

Seiji Shirakawa1, Shū Kobayashi.   

Abstract

A protocol for the dehydrative nucleophilic substitution of benzyl alcohols with a variety of carbon- and heteroatom-centered nucleophiles using dodecylbenzenesulfonic acid (DBSA) as a surfactant-type Brønsted acid catalyst in water has been developed. The reaction system can be applied to the stereoselective C-glycosylation of 1-hydroxy sugars in water. [reaction: see text].

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Year:  2007        PMID： 17217292     DOI： 10.1021/ol062813j

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Palladium-Catalyzed Direct α-Aryation of Benzyl Thioethers with Aryl Bromides.

Authors:  Gustavo Frensch; Nusrah Hussain; Francisco A Marques; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

2.  Efficient access to general α-tertiary amines via water-accelerated organocatalytic multicomponent allylation.

Authors:  Prithwish Goswami; Sung Yeon Cho; Jin Hyun Park; Woo Hee Kim; Hyun Jin Kim; Myoung Hyeon Shin; Han Yong Bae
Journal:  Nat Commun       Date:  2022-05-16       Impact factor: 17.694

3.  Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents.

Authors:  Mary M Rozenman; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-11-10       Impact factor: 15.419

4.  A review of new developments in the Friedel-Crafts alkylation - From green chemistry to asymmetric catalysis.

Authors:  Magnus Rueping; Boris J Nachtsheim
Journal:  Beilstein J Org Chem       Date:  2010-01-20       Impact factor: 2.883

Review 5.  Direct Dehydrative Glycosylation of C1-Alcohols.

Authors:  Sloane O'Neill; Jacob Rodriguez; Maciej A Walczak
Journal:  Chem Asian J       Date:  2018-10-01

6.  Biocompatible ionic liquid [Betaine][H2PO4] as a reusable catalyst for the substitution of xanthen-9-ol under solvent-free conditions.

Authors:  Anlian Zhu; Tong Wang; Wanlu Feng; Jianji Wang; Lingjun Li
Journal:  RSC Adv       Date:  2020-08-27       Impact factor: 4.036

Review 7.  Direct Substitution of Alcohols in Pure Water by Brønsted Acid Catalysis.

Authors:  Rosa Ortiz; Raquel P Herrera
Journal:  Molecules       Date:  2017-04-01       Impact factor: 4.411

8.  B(C6F5)3 catalyzed direct nucleophilic substitution of benzylic alcohols: an effective method of constructing C-O, C-S and C-C bonds from benzylic alcohols.

Authors:  Shan-Shui Meng; Qian Wang; Gong-Bin Huang; Li-Rong Lin; Jun-Ling Zhao; Albert S C Chan
Journal:  RSC Adv       Date:  2018-09-03       Impact factor: 3.361

9.  Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes.

Authors:  H Surya Prakash Rao; A Veera Bhadra Rao
Journal:  Beilstein J Org Chem       Date:  2016-03-11       Impact factor: 2.883
  9 in total

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