Phosphine Borane Frustrated Lewis Pairs Derived from a 1,1'-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis
Result description
(Dimesitylphosphino)ferrocene (FcPMes2) (1) reacted with HB(C6F5)2 (2 equiv) by disproportionation to give adduct FcPMes2*H2B(C6F5) (4) plus B(C6F5)3, whereas 1-(dimesitylphosphino)-1'-vinylferrocene (2) was cleanly hydroborated with HB(C6F5)2 to afford [Fe(eta(5)-C5H4PMes2)(eta5-C5H4CH2CH2B(C6F5)2)] (7). Compound 7 adopted an open non-interacting P/B frustrated Lewis pair (FLP) structure in the crystal state as well as in a solution. This frustrated Lewis pair heterolytically cleaved dihydrogen under mild conditions to give the respective zwitterionic [P]H+/[B]H- phosphonium/hydroborate product, [Fe(eta(5)-C5H4PHMes2){eta(5)-C5H4CH2CH2BH(C6F5)2}] (8), which served as a catalyst for the hydrogenation of the electron-rich pi-systems (imine, enamine) as well as well as the electron-deficient carbon carbon double and triple bonds in some enones and an ynone under more forcing conditions (50 bar H-2 pressure, 50 degrees C).
Keywords
The result's identifiers
Result code in IS VaVaI
Result on the web
DOI - Digital Object Identifier
Alternative languages
Result language
angličtina
Original language name
Phosphine Borane Frustrated Lewis Pairs Derived from a 1,1'-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis
Original language description
(Dimesitylphosphino)ferrocene (FcPMes2) (1) reacted with HB(C6F5)2 (2 equiv) by disproportionation to give adduct FcPMes2*H2B(C6F5) (4) plus B(C6F5)3, whereas 1-(dimesitylphosphino)-1'-vinylferrocene (2) was cleanly hydroborated with HB(C6F5)2 to afford [Fe(eta(5)-C5H4PMes2)(eta5-C5H4CH2CH2B(C6F5)2)] (7). Compound 7 adopted an open non-interacting P/B frustrated Lewis pair (FLP) structure in the crystal state as well as in a solution. This frustrated Lewis pair heterolytically cleaved dihydrogen under mild conditions to give the respective zwitterionic [P]H+/[B]H- phosphonium/hydroborate product, [Fe(eta(5)-C5H4PHMes2){eta(5)-C5H4CH2CH2BH(C6F5)2}] (8), which served as a catalyst for the hydrogenation of the electron-rich pi-systems (imine, enamine) as well as well as the electron-deficient carbon carbon double and triple bonds in some enones and an ynone under more forcing conditions (50 bar H-2 pressure, 50 degrees C).
Czech name
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Czech description
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Classification
Type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10402 - Inorganic and nuclear chemistry
Result continuities
Project
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organometallics
ISSN
0276-7333
e-ISSN
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Volume of the periodical
36
Issue of the periodical within the volume
15
Country of publishing house
US - UNITED STATES
Number of pages
7
Pages from-to
2940-2946
UT code for WoS article
000407869100028
EID of the result in the Scopus database
2-s2.0-85027404745
Result type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
OECD FORD
Inorganic and nuclear chemistry
Year of implementation
2017