Chapter 1
Frustrated Lewis Pair Catalysis:
An Introduction
Douglas W. Stephan
Abstract This chapter provides a brief overview of the evolution of FLP catalysis.
We begin with a description of the initial finding of reversible hydrogen activation
and the development of FLP-mediated catalytic hydrogenations. Subsequently, the
applications of FLPs in other catalytic processes involving other small molecules are
considered. These include hydrosilylation, transfer hydrogenations, hydroboration,
amination, hydroarylation, C–H borylation, polymerization, CO 2 reduction, and C–F
derivatization. The chapter concludes with a summary and short discussion of future
potential.
Keywords Frustrated lewis pairs · Hydrogenation · Hydrosilylation · Transfer
hydrogenations · Hydroboration · Amination · Hydroarylation · C–H borylation ·
Polymerization · CO 2 reduction · C–F derivatization
Abbreviations
9-BBN
9-Borabicyclo[3.3.1]nonane
Ar
Aryl
atm
Atmosphere
bipy
Bipyridine
Bn
Benzyl
Bu
Butyl
cat
Catechol
Cat.
Catalyst
Cp
Cyclopentadienide
Cy
Cyclohexyl
DABCO
1,4-Diazabicyclo[2.2.2]octane
EPC
Electrophilic phosphonium cation
D. W. Stephan (B)
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M6S3H6, Canada
e-mail: dstephan@chem.utoronto.ca
© Springer Nature Switzerland AG 2021
J. Chris Slootweg and A. R. Jupp (eds.), Frustrated Lewis Pairs,
Molecular Catalysis 2, https://doi.org/10.1007/978-3-030-58888-5_1
1
Frustrated Lewis Pair Catalysis:
An Introduction
Douglas W. Stephan
Abstract This chapter provides a brief overview of the evolution of FLP catalysis.
We begin with a description of the initial finding of reversible hydrogen activation
and the development of FLP-mediated catalytic hydrogenations. Subsequently, the
applications of FLPs in other catalytic processes involving other small molecules are
considered. These include hydrosilylation, transfer hydrogenations, hydroboration,
amination, hydroarylation, C–H borylation, polymerization, CO 2 reduction, and C–F
derivatization. The chapter concludes with a summary and short discussion of future
potential.
Keywords Frustrated lewis pairs · Hydrogenation · Hydrosilylation · Transfer
hydrogenations · Hydroboration · Amination · Hydroarylation · C–H borylation ·
Polymerization · CO 2 reduction · C–F derivatization
Abbreviations
9-BBN
9-Borabicyclo[3.3.1]nonane
Ar
Aryl
atm
Atmosphere
bipy
Bipyridine
Bn
Benzyl
Bu
Butyl
cat
Catechol
Cat.
Catalyst
Cp
Cyclopentadienide
Cy
Cyclohexyl
DABCO
1,4-Diazabicyclo[2.2.2]octane
EPC
Electrophilic phosphonium cation
D. W. Stephan (B)
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M6S3H6, Canada
e-mail: dstephan@chem.utoronto.ca
© Springer Nature Switzerland AG 2021
J. Chris Slootweg and A. R. Jupp (eds.), Frustrated Lewis Pairs,
Molecular Catalysis 2, https://doi.org/10.1007/978-3-030-58888-5_1
1