Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate

Annika C. J. Heinrich; Birk Thiedemann; Paul J. Gates; Anne Staubitz

doi:10.1021/ol401923j

Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate

Annika C. J. Heinrich, Birk Thiedemann, Paul J. Gates, Anne Staubitz^*

^*Corresponding author for this work

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

31 Citations (Scopus)

Abstract

The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.

Original language	English
Pages (from-to)	4666-4669
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	18
DOIs	https://doi.org/10.1021/ol401923j
Publication status	Published - 20 Sep 2013

Keywords

FACILE STEREOSELECTIVE-SYNTHESIS
HIGHLY EFFICIENT SYNTHESIS
DIFUNCTIONALIZED 1,3-DIENES
MOLECULAR DESIGN
POLYMERIZATION
POLYTHIOPHENES
HETEROCYCLES
COPOLYMERS
FLUORENE
SUZUKI

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@article{397ca23f93f34a398bf53adfff351e37,

title = "Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate",

abstract = "The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.",

keywords = "FACILE STEREOSELECTIVE-SYNTHESIS, HIGHLY EFFICIENT SYNTHESIS, DIFUNCTIONALIZED 1,3-DIENES, MOLECULAR DESIGN, POLYMERIZATION, POLYTHIOPHENES, HETEROCYCLES, COPOLYMERS, FLUORENE, SUZUKI",

author = "Heinrich, {Annika C. J.} and Birk Thiedemann and Gates, {Paul J.} and Anne Staubitz",

year = "2013",

month = sep,

day = "20",

doi = "10.1021/ol401923j",

language = "English",

volume = "15",

pages = "4666--4669",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate

AU - Heinrich, Annika C. J.

AU - Thiedemann, Birk

AU - Gates, Paul J.

AU - Staubitz, Anne

PY - 2013/9/20

Y1 - 2013/9/20

N2 - The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.

AB - The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.

KW - FACILE STEREOSELECTIVE-SYNTHESIS

KW - HIGHLY EFFICIENT SYNTHESIS

KW - DIFUNCTIONALIZED 1,3-DIENES

KW - MOLECULAR DESIGN

KW - POLYMERIZATION

KW - POLYTHIOPHENES

KW - HETEROCYCLES

KW - COPOLYMERS

KW - FLUORENE

KW - SUZUKI

U2 - 10.1021/ol401923j

DO - 10.1021/ol401923j

M3 - Article (Academic Journal)

C2 - 23980843

VL - 15

SP - 4666

EP - 4669

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 18

ER -

Dual Selectivity: Electrophile and Nucleophile Selective Cross-Coupling Reactions on a Single Aromatic Substrate

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Keywords

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