Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures

Peter G Wilson, Jonathan M Percy, Joanna Redmond, Adam W. McCarter

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A recently developed method for the nearambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1 - i o d o e t h e n e and 2 , 2 - d i fl u o r o - 1 - i o d o - 1 - ( 2 ′ -
methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki−Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.
LanguageEnglish
Pages6384-6393
Number of pages10
JournalJournal of Organic Chemistry
Volume77
Issue number15
DOIs
Publication statusPublished - 3 Aug 2012

Fingerprint

Derivatives
Potassium
Temperature
ethylene

Keywords

  • coupling yields
  • Suzuki–Miyaura couplings
  • potassium trifluoroborate
  • solvents

Cite this

Wilson, Peter G ; Percy, Jonathan M ; Redmond, Joanna ; McCarter, Adam W. / Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 15. pp. 6384-6393.
@article{27e6ff0ead2944e8a3c8c5cd1318db47,
title = "Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures",
abstract = "A recently developed method for the nearambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1 - i o d o e t h e n e and 2 , 2 - d i fl u o r o - 1 - i o d o - 1 - ( 2 ′ - methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki−Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.",
keywords = "coupling yields, Suzuki–Miyaura couplings, potassium trifluoroborate, solvents",
author = "Wilson, {Peter G} and Percy, {Jonathan M} and Joanna Redmond and McCarter, {Adam W.}",
year = "2012",
month = "8",
day = "3",
doi = "10.1021/jo3011705",
language = "English",
volume = "77",
pages = "6384--6393",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "15",

}

Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures. / Wilson, Peter G; Percy, Jonathan M; Redmond, Joanna; McCarter, Adam W.

In: Journal of Organic Chemistry, Vol. 77, No. 15, 03.08.2012, p. 6384-6393.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Suzuki−Miyaura coupling reactions of iodo(difluoroenol) derivatives, fluorinated building blocks accessible at near-ambient temperatures

AU - Wilson, Peter G

AU - Percy, Jonathan M

AU - Redmond, Joanna

AU - McCarter, Adam W.

PY - 2012/8/3

Y1 - 2012/8/3

N2 - A recently developed method for the nearambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1 - i o d o e t h e n e and 2 , 2 - d i fl u o r o - 1 - i o d o - 1 - ( 2 ′ - methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki−Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.

AB - A recently developed method for the nearambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1 - i o d o e t h e n e and 2 , 2 - d i fl u o r o - 1 - i o d o - 1 - ( 2 ′ - methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki−Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.

KW - coupling yields

KW - Suzuki–Miyaura couplings

KW - potassium trifluoroborate

KW - solvents

UR - http://www.scopus.com/inward/record.url?scp=84864608135&partnerID=8YFLogxK

U2 - 10.1021/jo3011705

DO - 10.1021/jo3011705

M3 - Article

VL - 77

SP - 6384

EP - 6393

JO - Journal of Organic Chemistry

T2 - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -