Carbocation Organocatalysis in Interrupted Povarov Reactions to cis-Fused Pyrano- and Furanobenzodihydropyrans

Jingjing Liu; Jiaxi Xu; Zhenjiang Li; Yu Huang; Haixin Wang; Yu Gao; Tianfo Guo; Pingkai Ouyang; Kai Guo

doi:10.1002/ejoc.201700634

Carbocation Organocatalysis in Interrupted Povarov Reactions to cis-Fused Pyrano- and Furanobenzodihydropyrans

Jingjing Liu, Jiaxi Xu, Zhenjiang Li, Yu Huang, Haixin Wang, Yu Gao, Tianfo Guo, Pingkai Ouyang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

23 Scopus citations

Abstract

Tritylium cation-catalyzed interrupted Povarov reactions afforded cis-4-aminobenzodihydropyrans in excellent yields (90 %) within 10 min by low catalyst loadings (1 mol-%). A mechanism involving Lewis acidic catalysis by a carbocation was proposed and validated. Changing a one-pot batch version of the reaction into a two-stage convergent continuous flow procedure led to a 10-fold time reduction (to 1 min) with 88 % yield.

Original language	English
Pages (from-to)	3996-4003
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.201700634
State	Published - 25 Jul 2017

Keywords

Carbocations
Heterocycles
Lewis acids
Organocatalysis
Povarov reaction
Tritylium ion

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10.1002/ejoc.201700634

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title = "Carbocation Organocatalysis in Interrupted Povarov Reactions to cis-Fused Pyrano- and Furanobenzodihydropyrans",

abstract = "Tritylium cation-catalyzed interrupted Povarov reactions afforded cis-4-aminobenzodihydropyrans in excellent yields (90 %) within 10 min by low catalyst loadings (1 mol-%). A mechanism involving Lewis acidic catalysis by a carbocation was proposed and validated. Changing a one-pot batch version of the reaction into a two-stage convergent continuous flow procedure led to a 10-fold time reduction (to 1 min) with 88 % yield.",

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author = "Jingjing Liu and Jiaxi Xu and Zhenjiang Li and Yu Huang and Haixin Wang and Yu Gao and Tianfo Guo and Pingkai Ouyang and Kai Guo",

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T1 - Carbocation Organocatalysis in Interrupted Povarov Reactions to cis-Fused Pyrano- and Furanobenzodihydropyrans

AU - Liu, Jingjing

AU - Xu, Jiaxi

AU - Li, Zhenjiang

AU - Huang, Yu

AU - Wang, Haixin

AU - Gao, Yu

AU - Guo, Tianfo

AU - Ouyang, Pingkai

AU - Guo, Kai

PY - 2017/7/25

Y1 - 2017/7/25

N2 - Tritylium cation-catalyzed interrupted Povarov reactions afforded cis-4-aminobenzodihydropyrans in excellent yields (90 %) within 10 min by low catalyst loadings (1 mol-%). A mechanism involving Lewis acidic catalysis by a carbocation was proposed and validated. Changing a one-pot batch version of the reaction into a two-stage convergent continuous flow procedure led to a 10-fold time reduction (to 1 min) with 88 % yield.

AB - Tritylium cation-catalyzed interrupted Povarov reactions afforded cis-4-aminobenzodihydropyrans in excellent yields (90 %) within 10 min by low catalyst loadings (1 mol-%). A mechanism involving Lewis acidic catalysis by a carbocation was proposed and validated. Changing a one-pot batch version of the reaction into a two-stage convergent continuous flow procedure led to a 10-fold time reduction (to 1 min) with 88 % yield.

KW - Carbocations

KW - Heterocycles

KW - Lewis acids

KW - Organocatalysis

KW - Povarov reaction

KW - Tritylium ion

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U2 - 10.1002/ejoc.201700634

DO - 10.1002/ejoc.201700634

M3 - 文章

AN - SCOPUS:85025679400

SN - 1434-193X

VL - 2017

SP - 3996

EP - 4003

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 27

ER -

Carbocation Organocatalysis in Interrupted Povarov Reactions to cis-Fused Pyrano- and Furanobenzodihydropyrans

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Keywords

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