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Trans-chloro-(1-naphthyl)bis[tris-(4-methoxyphenyl)phosphane]-nickel(II) catalyzed Suzuki-Miyaura coupling of aryl chlorides with phenylboronic acid

Paper ID Volume ID Publish Year Pages File Format Full-Text
50662 46806 2014 5 PDF Available
Title
Trans-chloro-(1-naphthyl)bis[tris-(4-methoxyphenyl)phosphane]-nickel(II) catalyzed Suzuki-Miyaura coupling of aryl chlorides with phenylboronic acid
Abstract

•NiCl(MOTPP)2(1-naphthyl) was prepared and applied successfully.•Excellent yields were achieved for the coupling of various aryl chlorides.•The impact of MOTPP was studied by single crystal X-ray diffraction.•The NiC and NiCl bonds in NiCl(MOTPP)2(1-naphthyl) were somewhat lengthened.•MOTPP increased the electron density of Ni compared to TPP.

A readily accessible trans-chloro-(1-naphthyl)bis-[tris-(4-methoxyphenyl)phosphine]-nickel(II) [NiCl(MOTPP)2(1-naphthyl)] complex was prepared and applied successfully to the Suzuki-Miyaura coupling of aryl chlorides with phenylboronic acid. The pre-catalyst readily forms the catalytically active Ni(0) species in situ under mild conditions without an additional reducing reagent. The electron-rich methoxy moieties on the phosphine ligand may increase the electron density of Ni and thus accelerates the reaction rate of oxidative addition. Single crystal X-ray diffraction revealed the NiCl and NiC bonds were lengthened in comparison with those in NiCl(PPh3)2(1-naphthyl), presumably owing to the stronger electron donating ability of MOTPP, which would facilitate the oxidative addition step.

Graphical abstractNiCl(MOTPP)2(1-naphthyl) could afford excellent yields (92–98%) within 1 h for the coupling of aryl chlorides bearing electron-withdrawing groups. Around 78–88% yields were observed for aryl chlorides with electron-donating or amino-substituents.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Suzuki-Miyaura coupling; Aryl chlorides; Nickel; Tris-(4-methoxyphenyl)phosphine
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Trans-chloro-(1-naphthyl)bis[tris-(4-methoxyphenyl)phosphane]-nickel(II) catalyzed Suzuki-Miyaura coupling of aryl chlorides with phenylboronic acid
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 57, 5 December 2014, Pages 143–147
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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