Brønsted acid catalyzed α-alkylation of aldehydes with diaryl methyl alcohols

Chong Xing; Hui Sun; Junmin Zhang; Guohui Li; Yonggui Robin Chi

doi:10.1002/chem.201102623

Brønsted acid catalyzed α-alkylation of aldehydes with diaryl methyl alcohols

Chong Xing, Hui Sun, Junmin Zhang, Guohui Li^*, Yonggui Robin Chi

^*Corresponding author for this work

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

21 Citations (Scopus)

Abstract

A proton does the two jobs: Brønsted acids alone catalyze the α-alkylation of aldehydes with diaryl alcohols. In this type of transformation, the acid-catalysis approach offers a broader substrate scope compared to the previously used enamine catalysis methods. The acid plays two important roles: one is to mediate the alcohol dehydration for carbocation formation; the other is to accelerate the rate-determining aldehyde enolization (see scheme).

Original language	English
Pages (from-to)	12272-12275
Number of pages	4
Journal	Chemistry - A European Journal
Volume	17
Issue number	44
DOIs	https://doi.org/10.1002/chem.201102623
Publication status	Published - Oct 24 2011
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Organic Chemistry

Keywords

alcohols
aldehydes
alkylation
Brønsted acid
carbocations

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10.1002/chem.201102623

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title = "Br{\o}nsted acid catalyzed α-alkylation of aldehydes with diaryl methyl alcohols",

abstract = "A proton does the two jobs: Br{\o}nsted acids alone catalyze the α-alkylation of aldehydes with diaryl alcohols. In this type of transformation, the acid-catalysis approach offers a broader substrate scope compared to the previously used enamine catalysis methods. The acid plays two important roles: one is to mediate the alcohol dehydration for carbocation formation; the other is to accelerate the rate-determining aldehyde enolization (see scheme).",

keywords = "alcohols, aldehydes, alkylation, Br{\o}nsted acid, carbocations",

author = "Chong Xing and Hui Sun and Junmin Zhang and Guohui Li and Chi, {Yonggui Robin}",

year = "2011",

month = oct,

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doi = "10.1002/chem.201102623",

language = "English",

volume = "17",

pages = "12272--12275",

journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - Brønsted acid catalyzed α-alkylation of aldehydes with diaryl methyl alcohols

AU - Xing, Chong

AU - Sun, Hui

AU - Zhang, Junmin

AU - Li, Guohui

AU - Chi, Yonggui Robin

PY - 2011/10/24

Y1 - 2011/10/24

N2 - A proton does the two jobs: Brønsted acids alone catalyze the α-alkylation of aldehydes with diaryl alcohols. In this type of transformation, the acid-catalysis approach offers a broader substrate scope compared to the previously used enamine catalysis methods. The acid plays two important roles: one is to mediate the alcohol dehydration for carbocation formation; the other is to accelerate the rate-determining aldehyde enolization (see scheme).

AB - A proton does the two jobs: Brønsted acids alone catalyze the α-alkylation of aldehydes with diaryl alcohols. In this type of transformation, the acid-catalysis approach offers a broader substrate scope compared to the previously used enamine catalysis methods. The acid plays two important roles: one is to mediate the alcohol dehydration for carbocation formation; the other is to accelerate the rate-determining aldehyde enolization (see scheme).

KW - alcohols

KW - aldehydes

KW - alkylation

KW - Brønsted acid

KW - carbocations

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EP - 12275

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 44

ER -

Brønsted acid catalyzed α-alkylation of aldehydes with diaryl methyl alcohols

Abstract

ASJC Scopus Subject Areas

Keywords

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