Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents

Dorus Heijnen; Filippo Tosi; Carlos Vila; Marc C. A. Stuart; Philip H. Elsinga; Wiktor Szymanski; Ben L. Feringa

doi:10.1002/anie.201700417

Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents

Dorus Heijnen, Filippo Tosi, Carlos Vila, Marc C. A. Stuart, Philip H. Elsinga, Wiktor Szymanski, Ben L. Feringa^*

^*Corresponding author for this work

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

62 Citations (Scopus)

173 Downloads (Pure)

Abstract

The discovery of an ultrafast cross-coupling of alkyland aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [C-11]-labeled PET tracer celecoxib.

Original language	English
Pages (from-to)	3354-3359
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	12
Early online date	14-Feb-2017
DOIs	https://doi.org/10.1002/anie.201700417
Publication status	Published - 13-Mar-2017

Keywords

cross-coupling
isotope labeling
nanoparticles
organolithium regents
palladium
CROSS-COUPLING REACTIONS
RAPID ROOM-TEMPERATURE
ARYLBORONIC ACIDS
PD NANOPARTICLES
CONTINUOUS-FLOW
ARYL CHLORIDES
SUPPORTED PD
COMPLEXES
HALIDES
METHYLLITHIUM

Access to Document

10.1002/anie.201700417

Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross- Coupling of Organolithium ReagentsFinal publisher's version, 2.21 MBLicence: Taverne

Handle.net

Persistent link

Cite this

@article{8d585194f9194588b54efb8543d94be3,

title = "Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents",

abstract = "The discovery of an ultrafast cross-coupling of alkyland aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [C-11]-labeled PET tracer celecoxib.",

keywords = "cross-coupling, isotope labeling, nanoparticles, organolithium regents, palladium, CROSS-COUPLING REACTIONS, RAPID ROOM-TEMPERATURE, ARYLBORONIC ACIDS, PD NANOPARTICLES, CONTINUOUS-FLOW, ARYL CHLORIDES, SUPPORTED PD, COMPLEXES, HALIDES, METHYLLITHIUM",

author = "Dorus Heijnen and Filippo Tosi and Carlos Vila and Stuart, {Marc C. A.} and Elsinga, {Philip H.} and Wiktor Szymanski and Feringa, {Ben L.}",

note = "{\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2017",

month = mar,

day = "13",

doi = "10.1002/anie.201700417",

language = "English",

volume = "56",

pages = "3354--3359",

journal = "Angewandte Chemie - International Edition",

issn = "1521-3773",

publisher = "WILEY-V C H VERLAG GMBH",

number = "12",

}

TY - JOUR

T1 - Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents

AU - Heijnen, Dorus

AU - Tosi, Filippo

AU - Vila, Carlos

AU - Stuart, Marc C. A.

AU - Elsinga, Philip H.

AU - Szymanski, Wiktor

AU - Feringa, Ben L.

PY - 2017/3/13

Y1 - 2017/3/13

N2 - The discovery of an ultrafast cross-coupling of alkyland aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [C-11]-labeled PET tracer celecoxib.

AB - The discovery of an ultrafast cross-coupling of alkyland aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross-coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [C-11]-labeled PET tracer celecoxib.

KW - cross-coupling

KW - isotope labeling

KW - nanoparticles

KW - organolithium regents

KW - palladium

KW - CROSS-COUPLING REACTIONS

KW - RAPID ROOM-TEMPERATURE

KW - ARYLBORONIC ACIDS

KW - PD NANOPARTICLES

KW - CONTINUOUS-FLOW

KW - ARYL CHLORIDES

KW - SUPPORTED PD

KW - COMPLEXES

KW - HALIDES

KW - METHYLLITHIUM

U2 - 10.1002/anie.201700417

DO - 10.1002/anie.201700417

M3 - Article

C2 - 28194863

SN - 1521-3773

VL - 56

SP - 3354

EP - 3359

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 12

ER -

Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Cite this