Nathan A. Eberhardt

University of Cincinnati

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Hairong Guan

University of Cincinnati

Jeanette A. Krause

University of Cincinnati

Wenjuan Meng

Chinese Academy of Sciences

Kendra M. Leahy

University of Cincinnati

Anubendu Adhikary

VIT-AP University

Qianyi Zhao

Henan Normal University

Qiuyu Yang

Jiangnan University

Xuenian Chen

Henan Normal University

Huizhen Li

Guangzhou University

Nana Ma

National Center for Nanoscience and Technology

Cooperative Institutions

Chinese Academy of Sciences

Henan Normal University

Universidad Nacional Autónoma de México

University of Chinese Academy of Sciences

University of Cincinnati

University of Warwick

Mississippi State University

University of East Anglia

Universidad de Zaragoza

Consejo Superior de Investigaciones Científicas

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Nickel Hydride Complexes

Chemical Reviews (2016)

Nathan A. Eberhardt Hairong Guan

Nickel hydride complexes, defined herein as any molecules bearing a nickel hydrogen bond, are crucial intermediates in numerous nickel-catalyzed reactions. Some of them are also synthetic models of nickel-containing enzymes such as [NiFe]-hydrogenase. The overall objective of this review is to provide a comprehensive overview of this specific type of hydride complexes, which has been studied extensively in recent years. This review begins with the significance and a very brief history of nickel hydride complexes, followed by various methods and spectroscopic or crystallographic tools used to synthesize and characterize these complexes. Also discussed are stoichiometric reactions involving nickel hydride complexes and how some of these reactions are developed into catalytic processes.

Hydrogenase

Stoichiometry

10.1021/acs.chemrev.6b00259

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Citations (302)

CCDC 1034585: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Huizhen Li Wenjuan Meng Anubendu Adhikary Shujun Li Nana Ma

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cc13qkq3

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Reduction of CO 2 Mediated or Catalyzed by Pincer Complexes

Elsevier eBooks (2018)

Nathan A. Eberhardt Hairong Guan

Hydrosilylation

10.1016/b978-0-12-812931-9.00004-9

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Synthesis and Reactivity of Nickel POCOP Pincer Complexes for the Reduction of Carbon Dioxide and Related Compounds

Nathan A. Eberhardt

Reactivity

Source

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Citations (1)

CCDC 1404906: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Huizhen Li Wenjuan Meng Anubendu Adhikary Shujun Li Nana Ma

10.5517/cc1j4xk4

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Dehydrogenative Coupling of Aldehydes with Alcohols Catalyzed by a Nickel Hydride Complex

Organometallics (2019)

Nathan A. Eberhardt Nadeesha P. N. Wellala Yingze Li Jeanette A. Krause Hairong Guan

A nickel hydride complex, {2,6-(iPr2PO)2C6H3}NiH, has been shown to catalyze the coupling of RCHO and R′OH to yield RCO2R′ and RCH2OH, where the aldehyde also acts as a hydrogen acceptor and the alcohol also serves as the solvent. Functional groups tolerated by this catalytic system include CF3, NO2, Cl, Br, NHCOMe, and NMe2, whereas phenol-containing compounds are not viable substrates or solvents. The dehydrogenative coupling reaction can alternatively be catalyzed by an air-stable nickel chloride complex, {2,6-(iPr2PO)2C6H3}NiCl, in conjunction with NaOMe. Acids in unpurified aldehydes react with the hydride to form nickel carboxylate complexes, which are catalytically inactive. Water, if present in a significant quantity, decreases the catalytic efficiency by forming {2,6-(iPr2PO)2C6H3}NiOH, which causes catalyst degradation. On the other hand, in the presence of a drying agent, {2,6-(iPr2PO)2C6H3}NiOH generated in situ from {2,6-(iPr2PO)2C6H3}NiCl and NaOH can be converted to an alkoxide species, becoming catalytically competent. The proposed catalytic mechanism features aldehyde insertion into the nickel hydride as well as into a nickel alkoxide intermediate, both of which have been experimentally observed. Several mechanistically relevant nickel species including {2,6-(iPr2PO)2C6H3}NiOC(O)Ph, {2,6-(iPr2PO)2C6H3}NiOPh, and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh have been independently synthesized, crystallographically characterized, and tested for the catalytic reaction. While phenol-containing molecules cannot be used as substrates or solvents, both {2,6-(iPr2PO)2C6H3}NiOPh and {2,6-(iPr2PO)2C6H3}NiOPh·HOPh are efficient in catalyzing the dehydrogenative coupling of PhCHO with EtOH.

Alkoxide

Sodium hydride

10.1021/acs.organomet.8b00888

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Citations (19)

CCDC 1881636: Experimental Crystal Structure Determination

The Cambridge Structural Database (2019)

Nathan A. Eberhardt Nadeesha P. N. Wellala Yingze Li Jeanette A. Krause Hairong Guan

10.5517/ccdc.csd.cc214zy4

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CCDC 1404903: Experimental Crystal Structure Determination