Synthesis 2016; 48(17): 2808-2815
DOI: 10.1055/s-0035-1562343
special topic
© Georg Thieme Verlag Stuttgart · New York

NiIICl(1-Naphthyl)(PCy3)2, An Air-Stable σ-NiII Precatalyst for Quantitative Cross-Coupling of Aryl C–O Electrophiles with Aryl Neopentylglycolboronates

Jagadeesh Malineni
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
,
Ryan L. Jezorek
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
,
Na Zhang
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
,
Virgil Percec*
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   Email: percec@sas.upenn.edu
› Author Affiliations
Further Information

Publication History

Received: 29 April 2016

Accepted after revision: 30 May 2016

Publication Date:
28 June 2016 (eFirst)

Abstract

Advances in nickel catalysis have enabled the employment of the widely available and environmentally benign phenol derivatives as aryl electrophiles in Suzuki–Miyaura cross-coupling reactions. NiII-phosphine complexes such as NiIICl2(PPh3)2, NiIICl2(dppf), NiIICl2(dppe), NiIICl2(dppp), NiIICl2(PCy3)2 and π-Ni0 complexes, the classic being Ni(COD)2/PCy3, both classes mostly in the presence of a mixed ligand, are some of the most successful precatalysts employed in the cross-coupling of aryl mesylates, sulfamates, carboxylic esters, carbonates, carbamates and methyl ethers with aryl boronic acids, boroxines and neopentylglycolboronates. Here we report that the highly reactive but bench-stable σ-NiII complex, NiIICl(1-naphthyl)(PCy3)2 (where σ refers to the Ni–C bond), exhibits higher efficiency than all previously reported precatalysts and facilitates the quantitative cross-coupling of all six C–O electrophiles mentioned above in reaction times of 0.5 to 24 hours.

Supporting Information

 
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