Facile synthesis of N-aryl phenothiazines and phenoxazines via Brønsted acid catalyzed C−H amination of arenes

N-aryl phenothiazines and phenoxazines are of significant importance in various disciplines throughout academia and industry. Conventional synthetic strategy for the construction of these structures centers on transition-metal-catalyzed cross-coupling of aryl...

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The electrophilic aromatic substitution approach to C–H silylation and C–H borylation

Pure and Applied Chemistry ◽

10.1515/pac-2017-0902 ◽

2018 ◽

Vol 90 (4) ◽

pp. 723-731 ◽

Cited By ~ 5

Author(s):

Susanne Bähr ◽

Martin Oestreich

Keyword(s):

Transition Metal ◽

Lewis Acid ◽

Electrophilic Aromatic Substitution ◽

Bronsted Acid ◽

Aromatic Substitution ◽

Brønsted Acid ◽

Brönsted Acid ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

AbstractSeveral approaches toward electrophilic C–H silylation of electron-rich arenes are discussed, comprising transition-metal-catalyzed processes as well as Lewis-acid- and Brønsted-acid-induced protocols. These methods differ in the catalytic generation of the silicon electrophile but share proton removal in form of dihydrogen. With slight modifications, these methods are often also applicable to the related electrophilic C–H borylation.

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Brønsted Acid Activation Strategy in Transition-Metal Catalyzed Asymmetric Hydrogenation of N-Unprotected Imines, Enamines, and N-Heteroaromatic Compounds

Angewandte Chemie International Edition ◽

10.1002/anie.201200963 ◽

2012 ◽

Vol 51 (25) ◽

pp. 6060-6072 ◽

Cited By ~ 141

Author(s):

Zhengkun Yu ◽

Weiwei Jin ◽

Quanbin Jiang

Keyword(s):

Transition Metal ◽

Asymmetric Hydrogenation ◽

Acid Activation ◽

Bronsted Acid ◽

Brønsted Acid ◽

Heteroaromatic Compounds ◽

Brönsted Acid ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

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Brønsted acid-catalyzed selective C–C bond cleavage of 1,3-diketones: a facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate

RSC Advances ◽

10.1039/c5ra17969f ◽

2015 ◽

Vol 5 (104) ◽

pp. 85646-85651 ◽

Cited By ~ 22

Author(s):

Guanshuo Shen ◽

Haifeng Zhou ◽

Peng Du ◽

Sensheng Liu ◽

Kun Zou ◽

...

Keyword(s):

Bond Cleavage ◽

Ethyl Lactate ◽

Bronsted Acid ◽

Brønsted Acid ◽

Facile Synthesis ◽

Brönsted Acid ◽

Acid Catalyzed

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Chiral Counteranions in Asymmetric Transition-Metal Catalysis: Highly Enantioselective Pd/Brønsted Acid-Catalyzed Direct α-Allylation of Aldehydes

Journal of the American Chemical Society ◽

10.1021/ja074678r ◽

2007 ◽

Vol 129 (37) ◽

pp. 11336-11337 ◽

Cited By ~ 455

Author(s):

Santanu Mukherjee ◽

Benjamin List

Keyword(s):

Transition Metal ◽

Transition Metal Catalysis ◽

Bronsted Acid ◽

Brønsted Acid ◽

Metal Catalysis ◽

Brönsted Acid ◽

Acid Catalyzed

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Facile Synthesis of Versatile Enantioenriched α-Substituted Hydroxy Esters through a Brønsted Acid Catalyzed Kinetic Resolution

Organic Letters ◽

10.1021/ol400207t ◽

2013 ◽

Vol 15 (6) ◽

pp. 1266-1269 ◽

Cited By ~ 42

Author(s):

Ghassan Qabaja ◽

Jennifer E. Wilent ◽

Amanda R. Benavides ◽

George E. Bullard ◽

Kimberly S. Petersen

Keyword(s):

Kinetic Resolution ◽

Bronsted Acid ◽

Brønsted Acid ◽

Facile Synthesis ◽

Brönsted Acid ◽

Hydroxy Esters ◽

Acid Catalyzed

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Brønsted acid-catalyzed facile synthesis of α-substituted N-arylaminoacetals and their downstream conversions to functionalized pyrroles

Molecular Catalysis ◽

10.1016/j.mcat.2019.02.010 ◽

2019 ◽

Vol 468 ◽

pp. 36-43 ◽

Cited By ~ 6

Author(s):

Jian Yang ◽

Xin Wang ◽

Ahmed El-Harairy ◽

Rongxian Bai ◽

Yanlong Gu

Keyword(s):

Bronsted Acid ◽

Brønsted Acid ◽

Facile Synthesis ◽

Brönsted Acid ◽

Acid Catalyzed

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Facile synthesis of 9H-pyrrolo[1,2-a]indoles via Brønsted acid catalyzed cascade reactions

Chemical Communications ◽

10.1039/c9cc07228d ◽

2019 ◽

Vol 55 (97) ◽

pp. 14613-14616 ◽

Cited By ~ 3

Author(s):

Kunhua Xu ◽

Wenming Chen ◽

Jin Lin ◽

Guifang Chen ◽

Biao Wang ◽

...

Keyword(s):

Cascade Reactions ◽

Cascade Reaction ◽

Bronsted Acid ◽

Acid System ◽

Brønsted Acid ◽

Facile Synthesis ◽

Brönsted Acid ◽

Acid Catalyzed

A Brønsted acid system promotes the Friedel–Crafts alkenylation/1,6-addition/condensation cascade reaction of ynones with indoles to access 9H-pyrrolo[1,2-a]indoles.

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Claisen Rearrangement Triggered by Brønsted Acid Catalyzed Alkyne Alkoxylation

Synlett ◽

10.1055/s-0040-1719866 ◽

2022 ◽

Author(s):

Long Li ◽

Long-Wu Ye ◽

Yao-Hong Yan

Keyword(s):

Claisen Rearrangement ◽

High Efficiency ◽

Rapid Development ◽

Bronsted Acid ◽

Brønsted Acid ◽

Diverse Range ◽

Claisen Rearrangements ◽

Brönsted Acid ◽

Acid Catalyzed ◽

Metal Catalyzed

AbstractOver the past two decades, catalytic alkyne alkoxylation-initiated Claisen rearrangement has proven to be a practical and powerful strategy for the rapid assembly of a diverse range of structurally complex molecules. The rapid development of Claisen rearrangements triggered by transition-metal-catalyzed alkyne alkoxylation has shown great potential in the formation of carbon–carbon bonds in an atom-economic and mild way. However, metal-free alkyne alkoxylation-triggered Claisen rearrangement has seldom been exploited. Recently, Brønsted acids such as HNTf2 and HOTf have been shown to be powerful activators that promote catalytic alkyne alkoxylation/Claisen rearrangement, leading to the concise and flexible synthesis of valuable compounds with high efficiency and atom economy. Recent advances on the Brønsted acid catalyzed alkyne alkoxylation/Claisen rearrangement are introduced in this Account, in which both intramolecular and intermolecular tandem reactions are discussed.

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