Copper-catalyzed oxidative heck reactions between alkyltrifluoroborates and vinyl arenes

Timothy W. Liwosz; Sherry R. Chemler

doi:10.1021/ol401220b

Copper-catalyzed oxidative heck reactions between alkyltrifluoroborates and vinyl arenes

Timothy W. Liwosz
, Sherry R. Chemler

Chemistry

SUNY Buffalo

Research output: Contribution to journal › Article › peer-review

92 Scopus citations

Abstract

We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)₂/1,10-phenanthroline with MnO₂ as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented.

Original language	English
Pages (from-to)	3034-3037
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	12
DOIs	https://doi.org/10.1021/ol401220b
State	Published - Jun 21 2013

Access to Document

10.1021/ol401220b

Cite this

@article{7c6e439339744808afd57af5d06ca2d5,

title = "Copper-catalyzed oxidative heck reactions between alkyltrifluoroborates and vinyl arenes",

abstract = "We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)2/1,10-phenanthroline with MnO2 as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented.",

author = "Liwosz, \{Timothy W.\} and Chemler, \{Sherry R.\}",

year = "2013",

month = jun,

day = "21",

doi = "10.1021/ol401220b",

language = "English",

volume = "15",

pages = "3034--3037",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Copper-catalyzed oxidative heck reactions between alkyltrifluoroborates and vinyl arenes

AU - Liwosz, Timothy W.

AU - Chemler, Sherry R.

PY - 2013/6/21

Y1 - 2013/6/21

N2 - We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)2/1,10-phenanthroline with MnO2 as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented.

AB - We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)2/1,10-phenanthroline with MnO2 as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented.

UR - https://www.scopus.com/pages/publications/84879356487

U2 - 10.1021/ol401220b

DO - 10.1021/ol401220b

M3 - Article

C2 - 23734764

AN - SCOPUS:84879356487

SN - 1523-7060

VL - 15

SP - 3034

EP - 3037

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Copper-catalyzed oxidative heck reactions between alkyltrifluoroborates and vinyl arenes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this