TY - JOUR
T1 - Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis
AU - Takise, Ryosuke
AU - Isshiki, Ryota
AU - Muto, Kei
AU - Itami, Kenichiro
AU - Yamaguchi, Junichiro
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant Number JP16H01011, and JP16H04148 (to J.Y.), the ERATO program from JST (to K.I.), the Early Bird Program of Waseda University (to K.M.), and a JSPS research fellowship for young scientists (to R.T.). We thank Dr. Yoshihiro Ishihara (Vertex Pharmaceuticals) for fruitful discussion and critical comments. ITbM is supported by the World Premier International Research Center (WPI) Initiative, Japan.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/3/8
Y1 - 2017/3/8
N2 - Because diaryl ethers are present as an important motif in pharmaceuticals and natural products, extensive studies for the development of novel methods have been conducted. A conventional method for the construction of the diaryl ether moiety is the intermolecular cross-coupling reaction of aryl halides and phenols with a copper or palladium catalyst. We developed a catalytic decarbonylative etherification of aromatic esters using a palladium or nickel catalyst with our enabling diphosphine ligand to give the corresponding diaryl ethers. The present reaction can be conducted on gram scale in excellent yield. This reaction not only functions in an intramolecular setting but also allows for a cross-etherification using other phenols.
AB - Because diaryl ethers are present as an important motif in pharmaceuticals and natural products, extensive studies for the development of novel methods have been conducted. A conventional method for the construction of the diaryl ether moiety is the intermolecular cross-coupling reaction of aryl halides and phenols with a copper or palladium catalyst. We developed a catalytic decarbonylative etherification of aromatic esters using a palladium or nickel catalyst with our enabling diphosphine ligand to give the corresponding diaryl ethers. The present reaction can be conducted on gram scale in excellent yield. This reaction not only functions in an intramolecular setting but also allows for a cross-etherification using other phenols.
UR - http://www.scopus.com/inward/record.url?scp=85014643847&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85014643847&partnerID=8YFLogxK
U2 - 10.1021/jacs.7b00049
DO - 10.1021/jacs.7b00049
M3 - Article
C2 - 28215077
AN - SCOPUS:85014643847
SN - 0002-7863
VL - 139
SP - 3340
EP - 3343
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 9
ER -