Download PDF
Synfacts 2016; 12(3): 0311
DOI: 10.1055/s-0035-1561683
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Suzuki Coupling with an N-Heterocyclic Carbene–Palladium Catalyst

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Fujihara T, * Yoshikawa T, Satou M, Ohta H, Terao J, Tsuji Y. * Kyoto University, Japan
N-Heterocyclic Carbene Ligands Bearing Poly(ethylene glycol) Chains: Effect of the Chain Length on Palladium-Catalyzed Coupling Reactions Employing Aryl Chlorides.

Chem. Commun. 2015;
51: 17382-17385
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
16 February 2016 (online)

 
 PDF Download Permissions and Reprints

Key words

N-heterocyclic carbenes - ligands - poly(ethylene glycol) - palladium - aryl chlorides - Suzuki coupling

Significance

N-Heterocyclic carbenes (NHCs) L bearing poly(ethylene glycol) chains promoted the palladium-catalyzed Suzuki–Miyaura coupling of aryl chlorides with arylboronic acids to give the corresponding biaryls in up to 96% yield (eq. 1). The borylation of aryl chlorides with B2pin2 also proceeded under similar catalytic conditions to afford the corresponding aryl boranes in up to 68% yield (eq. 2).


#

Comment

In the reaction of chlorotoluene with phenylboronic acid, the catalytic performance of L (n ≈ 17) was superior to that of other NHC ligands, such as IMes or IPr, and to NHC ligands L with shorter poly(ethylene glycol) chains (n = 0, 4, ~12).


#
#


   Permissions and Reprints