Ni(bpy)(cod): A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines

Amanda E. King; S. Chantal E. Stieber; Neil J. Henson; Stosh A. Kozimor; Brian L. Scott; Nathan C. Smythe; Andrew D. Sutton; John C. Gordon

doi:10.1002/ejic.201600143

Ni(bpy)(cod): A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines

Amanda E. King, S. Chantal E. Stieber, Neil J. Henson, Stosh A. Kozimor, Brian L. Scott, Nathan C. Smythe, Andrew D. Sutton, John C. Gordon

Research output: Contribution to journal › Article › peer-review

62 Scopus citations

Abstract

The catalytic hydroboration of ketones, aldehydes, and imines with pinacol borane and Ni(bpy)(cod) has been demonstrated in benzene at room temperature and low catalyst loadings (0.03-0.3 mol-%). Spectroscopic and structural evidence support the formulation of Ni(bpy)(cod) as containing a Ni^I cation and a bpy^·- ligand. The Ni(bpy)(cod) complex reacts quickly with ketonic substrates to form an adduct that appears to function as an entryway into catalytic activity.

Original language	English
Pages (from-to)	1635-1640
Number of pages	6
Journal	European Journal of Inorganic Chemistry
Volume	2016
Issue number	11
DOIs	https://doi.org/10.1002/ejic.201600143
State	Published - Apr 1 2016
Externally published	Yes

Funding

The authors thank the Laboratory Directed Research and Development (LDRD) program for a Director's Postdoctoral Fellowship to A. E. K. S. C. E. S. was supported by a LANL Glenn T. Seaborg Institute Postdoctoral Fellowship and by startup funding from the College of Science at the California State Polytechnic University, Pomona. Additional funding was provided by the under the Heavy Element Chemistry Program at LANL by the Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, U.S. Department of Energy (grants to S. A. K., S. C. E. S.). Los Alamos National Laboratory is operated by Los Alamos National Security, LLC, for the National Nuclear Security Administration of U.S. Department of Energy (contract DE-AC52-06NA25396).

Funders	Funder number
College of Science
LANL Glenn T. Seaborg Institute
U.S. Department of Energy
Basic Energy Sciences
National Nuclear Security Administration	DE-AC52-06NA25396
Laboratory Directed Research and Development
California State Polytechnic University, Pomona
Chemical Sciences, Geosciences, and Biosciences Division
Glenn T. Seaborg Institute
College of Science, University of Arizona

Keywords

Electronic structure
Homogeneous catalysis
Hydroboration
Nickel
Redox chemistry

Access to Document

10.1002/ejic.201600143

Cite this

@article{1d7ab41a7b314a3b8c5ae9b501020819,

title = "Ni(bpy)(cod): A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines",

abstract = "The catalytic hydroboration of ketones, aldehydes, and imines with pinacol borane and Ni(bpy)(cod) has been demonstrated in benzene at room temperature and low catalyst loadings (0.03-0.3 mol-%). Spectroscopic and structural evidence support the formulation of Ni(bpy)(cod) as containing a NiI cation and a bpy·- ligand. The Ni(bpy)(cod) complex reacts quickly with ketonic substrates to form an adduct that appears to function as an entryway into catalytic activity.",

keywords = "Electronic structure, Homogeneous catalysis, Hydroboration, Nickel, Redox chemistry",

author = "King, {Amanda E.} and Stieber, {S. Chantal E.} and Henson, {Neil J.} and Kozimor, {Stosh A.} and Scott, {Brian L.} and Smythe, {Nathan C.} and Sutton, {Andrew D.} and Gordon, {John C.}",

note = "Publisher Copyright: Copyright {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = apr,

day = "1",

doi = "10.1002/ejic.201600143",

language = "English",

volume = "2016",

pages = "1635--1640",

journal = "European Journal of Inorganic Chemistry",

issn = "1434-1948",

publisher = "Wiley-VCH Verlag",

number = "11",

}

TY - JOUR

T1 - Ni(bpy)(cod)

T2 - A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines

AU - King, Amanda E.

AU - Stieber, S. Chantal E.

AU - Henson, Neil J.

AU - Kozimor, Stosh A.

AU - Scott, Brian L.

AU - Smythe, Nathan C.

AU - Sutton, Andrew D.

AU - Gordon, John C.

PY - 2016/4/1

Y1 - 2016/4/1

N2 - The catalytic hydroboration of ketones, aldehydes, and imines with pinacol borane and Ni(bpy)(cod) has been demonstrated in benzene at room temperature and low catalyst loadings (0.03-0.3 mol-%). Spectroscopic and structural evidence support the formulation of Ni(bpy)(cod) as containing a NiI cation and a bpy·- ligand. The Ni(bpy)(cod) complex reacts quickly with ketonic substrates to form an adduct that appears to function as an entryway into catalytic activity.

AB - The catalytic hydroboration of ketones, aldehydes, and imines with pinacol borane and Ni(bpy)(cod) has been demonstrated in benzene at room temperature and low catalyst loadings (0.03-0.3 mol-%). Spectroscopic and structural evidence support the formulation of Ni(bpy)(cod) as containing a NiI cation and a bpy·- ligand. The Ni(bpy)(cod) complex reacts quickly with ketonic substrates to form an adduct that appears to function as an entryway into catalytic activity.

KW - Electronic structure

KW - Homogeneous catalysis

KW - Hydroboration

KW - Nickel

KW - Redox chemistry

UR - http://www.scopus.com/inward/record.url?scp=84961267051&partnerID=8YFLogxK

U2 - 10.1002/ejic.201600143

DO - 10.1002/ejic.201600143

M3 - Article

AN - SCOPUS:84961267051

SN - 1434-1948

VL - 2016

SP - 1635

EP - 1640

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 11

ER -

Ni(bpy)(cod): A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines

Abstract

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Cite this