Chemoselective Cross-Coupling Reactions with Differentiation between Two Nucleophilic Sites on a Single Aromatic Substrate

Julian Linshoeft; Annika C. J. Heinrich; Stephan A. W. Segler; Paul J. Gates; Anne Staubitz

doi:10.1021/ol302571t

Chemoselective Cross-Coupling Reactions with Differentiation between Two Nucleophilic Sites on a Single Aromatic Substrate

Julian Linshoeft, Annika C. J. Heinrich, Stephan A. W. Segler, Paul J. Gates, Anne Staubitz^*

^*Corresponding author for this work

School of Chemistry

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

45 Citations (Scopus)

Abstract

A new thiophene building block, containing both a stannyl group and a boronic ester, was prepared. From this starting material, a general, nucleophile-selective one-pot reaction was developed, exploiting the different reactivities of the Stille and Suzuki-Miyaura cross-coupling reactions. A series of aromatic electrophiles were used to demonstrate the high functional group tolerance.

Original language	English
Pages (from-to)	5644-5647
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	22
DOIs	https://doi.org/10.1021/ol302571t
Publication status	Published - 16 Nov 2012

Keywords

OLIGO(HET)ARYLENE BUILDING-BLOCKS
FACILE STEREOSELECTIVE-SYNTHESIS
HIGHLY EFFICIENT SYNTHESIS
THIN-FILM TRANSISTORS
DIFUNCTIONALIZED 1,3-DIENES
MOLECULAR DESIGN
SOLAR-CELLS
SUZUKI
THIOPHENE
HECK

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@article{56f48843add14db98110cd059ccd3ca7,

title = "Chemoselective Cross-Coupling Reactions with Differentiation between Two Nucleophilic Sites on a Single Aromatic Substrate",

abstract = "A new thiophene building block, containing both a stannyl group and a boronic ester, was prepared. From this starting material, a general, nucleophile-selective one-pot reaction was developed, exploiting the different reactivities of the Stille and Suzuki-Miyaura cross-coupling reactions. A series of aromatic electrophiles were used to demonstrate the high functional group tolerance.",

keywords = "OLIGO(HET)ARYLENE BUILDING-BLOCKS, FACILE STEREOSELECTIVE-SYNTHESIS, HIGHLY EFFICIENT SYNTHESIS, THIN-FILM TRANSISTORS, DIFUNCTIONALIZED 1,3-DIENES, MOLECULAR DESIGN, SOLAR-CELLS, SUZUKI, THIOPHENE, HECK",

author = "Julian Linshoeft and Heinrich, {Annika C. J.} and Segler, {Stephan A. W.} and Gates, {Paul J.} and Anne Staubitz",

year = "2012",

month = nov,

day = "16",

doi = "10.1021/ol302571t",

language = "English",

volume = "14",

pages = "5644--5647",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Chemoselective Cross-Coupling Reactions with Differentiation between Two Nucleophilic Sites on a Single Aromatic Substrate

AU - Linshoeft, Julian

AU - Heinrich, Annika C. J.

AU - Segler, Stephan A. W.

AU - Gates, Paul J.

AU - Staubitz, Anne

PY - 2012/11/16

Y1 - 2012/11/16

N2 - A new thiophene building block, containing both a stannyl group and a boronic ester, was prepared. From this starting material, a general, nucleophile-selective one-pot reaction was developed, exploiting the different reactivities of the Stille and Suzuki-Miyaura cross-coupling reactions. A series of aromatic electrophiles were used to demonstrate the high functional group tolerance.

AB - A new thiophene building block, containing both a stannyl group and a boronic ester, was prepared. From this starting material, a general, nucleophile-selective one-pot reaction was developed, exploiting the different reactivities of the Stille and Suzuki-Miyaura cross-coupling reactions. A series of aromatic electrophiles were used to demonstrate the high functional group tolerance.

KW - OLIGO(HET)ARYLENE BUILDING-BLOCKS

KW - FACILE STEREOSELECTIVE-SYNTHESIS

KW - HIGHLY EFFICIENT SYNTHESIS

KW - THIN-FILM TRANSISTORS

KW - DIFUNCTIONALIZED 1,3-DIENES

KW - MOLECULAR DESIGN

KW - SOLAR-CELLS

KW - SUZUKI

KW - THIOPHENE

KW - HECK

U2 - 10.1021/ol302571t

DO - 10.1021/ol302571t

M3 - Article (Academic Journal)

C2 - 23121649

SN - 1523-7060

VL - 14

SP - 5644

EP - 5647

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Chemoselective Cross-Coupling Reactions with Differentiation between Two Nucleophilic Sites on a Single Aromatic Substrate

Abstract

Keywords

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