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

Research output: Contribution to journal › Article (Academic Journal) › peer-review

119 Citations (Scopus)

455 Downloads (Pure)

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

Research Groups and Themes

Organic & Biological

Access to Document

10.1021/jacs.5b07842

Full-text PDF (final published version)
This is the final published version of the article (version of record). It first appeared online via American Chemical Society at http://dx.doi.org/10.1021/jacs.5b07842. Please refer to any applicable terms of use of the publisher.
Final published version, 1.19 MBLicence: CC BY

Handle.net

Persistent link

Cite this

@article{f15d6f86884543ddb9d9bf81a0f126a2,

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.",

author = "Josep Llaveria and Daniele Leonori and Aggarwal, \{Varinder K.\}",

year = "2015",

month = sep,

day = "2",

doi = "10.1021/jacs.5b07842",

language = "English",

volume = "137",

pages = "10958--10961",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "34",

}

TY - JOUR

T1 - Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

AU - Llaveria, Josep

AU - Leonori, Daniele

AU - Aggarwal, Varinder K.

PY - 2015/9/2

Y1 - 2015/9/2

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.

UR - https://www.scopus.com/pages/publications/84941010141

U2 - 10.1021/jacs.5b07842

DO - 10.1021/jacs.5b07842

M3 - Article (Academic Journal)

C2 - 26292943

AN - SCOPUS:84941010141

SN - 0002-7863

VL - 137

SP - 10958

EP - 10961

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 34

ER -

Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

Abstract

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

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

Cite this

Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

Abstract

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

3-month Core Capability for Chemistry Research

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

Profiles

Professor Varinder K Aggarwal

Cite this