Tritylium Cation as Low Loading Lewis Acidic Organocatalyst in Povarov Reactions

Yu Huang; Chuanhong Qiu; Zhenjiang Li; Weiyang Feng; Haifeng Gan; Jingjing Liu; Kai Guo

doi:10.1021/acssuschemeng.5b01379

Tritylium Cation as Low Loading Lewis Acidic Organocatalyst in Povarov Reactions

Yu Huang, Chuanhong Qiu, Zhenjiang Li, Weiyang Feng, Haifeng Gan, Jingjing Liu, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

Abstract

Triphenylmethylium cation catalyzed Povarov reactions with excellent yields in 1 h with a remarkably low loading (0.5 mol %) are disclosed. A Lewis acidic carbenium catalysis mechanism was proposed and validated. A three-component Povarov reaction in a batch was transferred into a two-stage microflow process, which resulted in a 60-fold reduction in reaction time from 2 h to 2 min with 89% separated yield.

Original language	English
Pages (from-to)	47-52
Number of pages	6
Journal	ACS Sustainable Chemistry and Engineering
Volume	4
Issue number	1
DOIs	https://doi.org/10.1021/acssuschemeng.5b01379
State	Published - 4 Jan 2016

Keywords

Carbenium
Low loading
Organocatalysis
Povarov reaction
Tetrahydroquinolines

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acssuschemeng.5b01379

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title = "Tritylium Cation as Low Loading Lewis Acidic Organocatalyst in Povarov Reactions",

abstract = "Triphenylmethylium cation catalyzed Povarov reactions with excellent yields in 1 h with a remarkably low loading (0.5 mol %) are disclosed. A Lewis acidic carbenium catalysis mechanism was proposed and validated. A three-component Povarov reaction in a batch was transferred into a two-stage microflow process, which resulted in a 60-fold reduction in reaction time from 2 h to 2 min with 89% separated yield.",

keywords = "Carbenium, Low loading, Organocatalysis, Povarov reaction, Tetrahydroquinolines",

author = "Yu Huang and Chuanhong Qiu and Zhenjiang Li and Weiyang Feng and Haifeng Gan and Jingjing Liu and Kai Guo",

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year = "2016",

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doi = "10.1021/acssuschemeng.5b01379",

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T1 - Tritylium Cation as Low Loading Lewis Acidic Organocatalyst in Povarov Reactions

AU - Huang, Yu

AU - Qiu, Chuanhong

AU - Li, Zhenjiang

AU - Feng, Weiyang

AU - Gan, Haifeng

AU - Liu, Jingjing

AU - Guo, Kai

PY - 2016/1/4

Y1 - 2016/1/4

N2 - Triphenylmethylium cation catalyzed Povarov reactions with excellent yields in 1 h with a remarkably low loading (0.5 mol %) are disclosed. A Lewis acidic carbenium catalysis mechanism was proposed and validated. A three-component Povarov reaction in a batch was transferred into a two-stage microflow process, which resulted in a 60-fold reduction in reaction time from 2 h to 2 min with 89% separated yield.

AB - Triphenylmethylium cation catalyzed Povarov reactions with excellent yields in 1 h with a remarkably low loading (0.5 mol %) are disclosed. A Lewis acidic carbenium catalysis mechanism was proposed and validated. A three-component Povarov reaction in a batch was transferred into a two-stage microflow process, which resulted in a 60-fold reduction in reaction time from 2 h to 2 min with 89% separated yield.

KW - Carbenium

KW - Low loading

KW - Organocatalysis

KW - Povarov reaction

KW - Tetrahydroquinolines

UR - http://www.scopus.com/inward/record.url?scp=84953300012&partnerID=8YFLogxK

U2 - 10.1021/acssuschemeng.5b01379

DO - 10.1021/acssuschemeng.5b01379

M3 - 文章

AN - SCOPUS:84953300012

SN - 2168-0485

VL - 4

SP - 47

EP - 52

JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

IS - 1

ER -

Tritylium Cation as Low Loading Lewis Acidic Organocatalyst in Povarov Reactions

Abstract

Keywords

UN SDGs

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