Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction

2013 ◽  
Vol 11 (9) ◽  
pp. 1533 ◽  
Author(s):  
Cyril Piemontesi ◽  
Qian Wang ◽  
Jieping Zhu
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
One Pot ◽  
Brönsted Acid ◽  
Brønsted Base ◽  
Acid Catalyzed

Brønsted Acid Catalyzed Dehydrative Nucleophilic Substitution of C3-Substituted 2-Indolylmethanols with Azlactones

Synthesis ◽  
2017 ◽  
Vol 50 (02) ◽  
pp. 295-302 ◽  
Author(s):  
Guang-Jian Mei ◽  
Feng Shi ◽  
Chen-Yu Bian ◽  
Dan Li ◽  
Qian Shi
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Direct Synthesis ◽  
Indole Derivatives ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Whole Process ◽  
Brönsted Acid ◽  
New Strategy ◽  
Acid Catalyzed

An efficient dehydrative nucleophilic substitution reaction of C3-substituted2-indolylmethanols with azlactones has been established. In the whole process, Brønsted acid was supposed to activate two substrates simultaneously. A series of structurally diversified indole derivatives were obtained in generally good yields and high diastereoselectivities (up to 86% yield, >95:5 dr). This protocol not only provides a new strategy for the direct synthesis of structurally diversified indole derivatives, but also enriches the chemistry of 2-indolylmethanols via dehydrative substitution reaction.

scholarly journals Brønsted acid-catalyzed metal-free one-pot synthesis of benzimidazoles via [4+1] heteroannulation of ortho-phenylenediamines with β-oxodithioesters

ARKIVOC ◽  
2017 ◽  
Vol 2018 (2) ◽  
pp. 81-89
Author(s):  
Abhijeet Srivastava ◽  
Gaurav Shukla ◽  
Dhananjay Yadav ◽  
Maya Shankar Singh
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Brönsted Acid ◽  
Acid Catalyzed

Brønsted Acid-Catalyzed Nucleophilic Substitution of Alcohols

2006 ◽  
Vol 348 (14) ◽  
pp. 1841-1845 ◽  
Author(s):  
Roberto Sanz ◽  
Alberto Martínez ◽  
Delia Miguel ◽  
Julia M. Álvarez-Gutiérrez ◽  
Félix Rodríguez
Keyword(s):  
Nucleophilic Substitution ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System

2010 ◽  
Vol 352 (17) ◽  
pp. 2881-2886 ◽  
Author(s):  
Alice Devineau ◽  
Guillaume Pousse ◽  
Catherine Taillier ◽  
Jérôme Blanchet ◽  
Jacques Rouden ◽  
...  
Keyword(s):  
Hydroxy Group ◽  
Bronsted Acid ◽  
Acid System ◽  
Brønsted Acid ◽  
One Pot ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Brönsted Acid ◽  
Brønsted Base

scholarly journals Chiral Brønsted acid-catalyzed intramolecular SN2′ reaction for enantioselective construction of a quaternary stereogenic center

2018 ◽  
Vol 9 (26) ◽  
pp. 5747-5757 ◽  
Author(s):  
Masahiro Shimizu ◽  
Jun Kikuchi ◽  
Azusa Kondoh ◽  
Masahiro Terada
Keyword(s):  
Substitution Reaction ◽  
Allylic Substitution ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Sn2 Reaction ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Stereogenic Center

Construction of a quaternary stereogenic center was accomplished through the enantioselective intramolecular allylic substitution reaction of bis-trichloroacetimidate catalyzed by a chiral phosphoramide derivative.

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