Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes

Ciril Jimeno; Sonia Sayalero; Torstein Fjermestad; Gisela Colet; Feliu Maseras; Miquel A. Pericàs

doi:10.1002/anie.200703103

Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes

Ciril Jimeno, Sonia Sayalero, Torstein Fjermestad, Gisela Colet, Feliu Maseras, Miquel A. Pericàs

Department of Chemistry

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

68 Citations (Scopus)

Abstract

(Chemical Equation Presented) Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Original language	English
Pages (from-to)	1098-1101
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	6
DOIs	https://doi.org/10.1002/anie.200703103
Publication status	Published - 11 Feb 2008

Keywords

Asymmetric catalysis
Boron
Density functional calculations
Reaction mechanisms
Zinc

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title = "Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes",

abstract = "(Chemical Equation Presented) Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data. {\textcopyright} 2008 Wiley-VCH Verlag GmbH & Co. KGaA.",

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Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes. / Jimeno, Ciril; Sayalero, Sonia; Fjermestad, Torstein; Colet, Gisela; Maseras, Feliu; Pericàs, Miquel A.

In: Angewandte Chemie - International Edition, Vol. 47, No. 6, 11.02.2008, p. 1098-1101.

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

TY - JOUR

T1 - Practical implications of boron-to-zinc transmetalation for the catalytic asymmetric arylation of aldehydes

AU - Jimeno, Ciril

AU - Sayalero, Sonia

AU - Fjermestad, Torstein

AU - Colet, Gisela

AU - Maseras, Feliu

AU - Pericàs, Miquel A.

PY - 2008/2/11

Y1 - 2008/2/11

N2 - (Chemical Equation Presented) Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

AB - (Chemical Equation Presented) Faster than believed: Transmetalation from aryl boronic acids and triaryl boroxines to diethylzinc takes place within minutes following a two-step, low-energy pathway (see picture), according to density functional calculations and reaction microcalorimetry measurements. The experimental conditions for a practical, atom-economical, and highly enantioselective catalytic arylation of a variety of aldehydes have been developed from these data. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

KW - Asymmetric catalysis

KW - Boron

KW - Density functional calculations

KW - Reaction mechanisms

KW - Zinc

U2 - 10.1002/anie.200703103

DO - 10.1002/anie.200703103

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VL - 47

SP - 1098

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 6

ER -