Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

Josep Llaveria; Daniele Leonori; Varinder K. Aggarwal

doi:10.1021/jacs.5b07842

Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

Josep Llaveria, Daniele Leonori, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

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Abstract

A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition of Troc-Cl, which activates the nitrogen and induces 1,2-migration. Oxidative workup furnishes the coupled product with >98% es.

Original language	English
Pages (from-to)	10958-10961
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	34
Early online date	21 Aug 2015
DOIs	https://doi.org/10.1021/jacs.5b07842
Publication status	Published - 2 Sept 2015

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title = "Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds",

abstract = "A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition of Troc-Cl, which activates the nitrogen and induces 1,2-migration. Oxidative workup furnishes the coupled product with >98% es.",

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N2 - A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition of Troc-Cl, which activates the nitrogen and induces 1,2-migration. Oxidative workup furnishes the coupled product with >98% es.

AB - A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition of Troc-Cl, which activates the nitrogen and induces 1,2-migration. Oxidative workup furnishes the coupled product with >98% es.

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Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

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3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Professor Varinder K Aggarwal

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Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

Abstract

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3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

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Professor Varinder K Aggarwal

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