NHC-Iron-Catalyzed Aerobic Oxidative Aromatic Esterification of Aldehydes using Boronic Acids

Joao N. Rosa; R. Sudarshan Reddy; Nuno R. Candeias; Pedro M. S. D. Cal; Pedro M. P. Gois

doi:10.1021/ol100302e

NHC-Iron-Catalyzed Aerobic Oxidative Aromatic Esterification of Aldehydes using Boronic Acids

Joao N. Rosa
, R. Sudarshan Reddy
, Nuno R. Candeias
, Pedro M. S. D. Cal
, Pedro M. P. Gois^*

^*Corresponding author for this work

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

79 Citations (Scopus)

Abstract

NHC Iron complexes prepared in situ very efficiently afforded benzoates via the aerobic oxidative aromatic esterification of aldehydes with boronic acids. This method uses equimolar amounts of both the aldehyde and the boronic acid allowing the preparation of benzoates in yields up to 97%.

Original language	English
Pages (from-to)	2686-2689
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	12
DOIs	https://doi.org/10.1021/ol100302e
Publication status	Published - 18 Jun 2010
Externally published	Yes
Publication type	A1 Journal article-refereed

Funding

The Fundacao para a Ciencia e Tecnologia and FEDER (PTDC/QUI-QUI/099389/2008; SFRH/BPD/46589/2008;/48219/2008;/65455/2009;REDE/1518/REM/2005) are thanked for the financial support.

Keywords

N-HETEROCYCLIC CARBENES
BAEYER-VILLIGER OXIDATION
CROSS-COUPLING REACTIONS
MOLECULAR-OXYGEN
ZINC-OXIDE
COMPLEXES
EFFICIENT
KETONES
ESTERS
POLYMERIZATION

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10.1021/ol100302e

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title = "NHC-Iron-Catalyzed Aerobic Oxidative Aromatic Esterification of Aldehydes using Boronic Acids",

abstract = "NHC Iron complexes prepared in situ very efficiently afforded benzoates via the aerobic oxidative aromatic esterification of aldehydes with boronic acids. This method uses equimolar amounts of both the aldehyde and the boronic acid allowing the preparation of benzoates in yields up to 97\%.",

keywords = "N-HETEROCYCLIC CARBENES, BAEYER-VILLIGER OXIDATION, CROSS-COUPLING REACTIONS, MOLECULAR-OXYGEN, ZINC-OXIDE, COMPLEXES, EFFICIENT, KETONES, ESTERS, POLYMERIZATION",

author = "Rosa, \{Joao N.\} and Reddy, \{R. Sudarshan\} and Candeias, \{Nuno R.\} and Cal, \{Pedro M. S. D.\} and Gois, \{Pedro M. P.\}",

year = "2010",

month = jun,

day = "18",

doi = "10.1021/ol100302e",

language = "English",

volume = "12",

pages = "2686--2689",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - NHC-Iron-Catalyzed Aerobic Oxidative Aromatic Esterification of Aldehydes using Boronic Acids

AU - Rosa, Joao N.

AU - Reddy, R. Sudarshan

AU - Candeias, Nuno R.

AU - Cal, Pedro M. S. D.

AU - Gois, Pedro M. P.

PY - 2010/6/18

Y1 - 2010/6/18

N2 - NHC Iron complexes prepared in situ very efficiently afforded benzoates via the aerobic oxidative aromatic esterification of aldehydes with boronic acids. This method uses equimolar amounts of both the aldehyde and the boronic acid allowing the preparation of benzoates in yields up to 97%.

AB - NHC Iron complexes prepared in situ very efficiently afforded benzoates via the aerobic oxidative aromatic esterification of aldehydes with boronic acids. This method uses equimolar amounts of both the aldehyde and the boronic acid allowing the preparation of benzoates in yields up to 97%.

KW - N-HETEROCYCLIC CARBENES

KW - BAEYER-VILLIGER OXIDATION

KW - CROSS-COUPLING REACTIONS

KW - MOLECULAR-OXYGEN

KW - ZINC-OXIDE

KW - COMPLEXES

KW - EFFICIENT

KW - KETONES

KW - ESTERS

KW - POLYMERIZATION

U2 - 10.1021/ol100302e

DO - 10.1021/ol100302e

M3 - Article

SN - 1523-7060

VL - 12

SP - 2686

EP - 2689

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

NHC-Iron-Catalyzed Aerobic Oxidative Aromatic Esterification of Aldehydes using Boronic Acids

Abstract

Funding

Keywords

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