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692573

Sigma-Aldrich

Bis(1,5-cyclooctadiene)rhodium(I) tetrakis[bis(3,5-trifluoromethyl)phenyl]borate

Synonym(s):

Bis(1,5-cyclooctadiene)rhodium BARF, Bis(1,5-cyclooctadiene)rhodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

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About This Item

Empirical Formula (Hill Notation):
C48H36BF24Rh
CAS Number:
404573-66-6
Molecular Weight:
1182.48
UNSPSC Code:
12161600
PubChem Substance ID:
329761509
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

core: rhodium
reagent type: catalyst

mp

155-156 °C (D)

storage temp.

−20°C

SMILES string

[Rh+].C1CC=CCCC=C1.C2CC=CCCC=C2.FC(F)(F)c3cc(cc(c3)C(F)(F)F)[B-](c4cc(cc(c4)C(F)(F)F)C(F)(F)F)(c5cc(cc(c5)C(F)(F)F)C(F)(F)F)c6cc(cc(c6)C(F)(F)F)C(F)(F)F

InChI

1S/C32H12BF24.2C8H12.Rh/c34-25(35,36)13-1-14(26(37,38)39)6-21(5-13)33(22-7-15(27(40,41)42)2-16(8-22)28(43,44)45,23-9-17(29(46,47)48)3-18(10-23)30(49,50)51)24-11-19(31(52,53)54)4-20(12-24)32(55,56)57;2*1-2-4-6-8-7-5-3-1;/h1-12H;2*1-2,7-8H,3-6H2;/q-1;;;+1/b;2*2-1-,8-7-;

InChI key

HQQAEXNVAYMZON-AUUWQFPRSA-N

Application

Bis(1,5-cyclooctadiene)rhodium(I) tetrakis[bis(3,5-trifluoromethyl)phenyl]borate can be used as a catalyst for various transformations, including hydrogenation, intramolecular C-H alkenylation, cycloaddition of enynes, and reductive coupling reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW2848
MKCV8508
03321AJ
10803TH

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Intramolecular C- H Alkenylation of N-Alkynylindoles: Exo and Endo Selective Cyclization According to the Choice of Metal Catalyst
Shibata, T, et al.
advanced synthesis and catalysis, 359(11), 1849-1853 (2017)
Proline-Based P, O Ligand/Iridium Complexes as Highly Selective Catalysts: Asymmetric Hydrogenation of Trisubstituted Alkenes
Rageot D, et al.
Angewandte Chemie (International Edition in English), 123(41), 9772-9775 (2011)
Highly diastereo-and enantioselective construction of both central and axial chiralities by Rh-catalyzed [2+ 2+ 2] cycloaddition
Shibata T, et al.
Organic & Biomolecular Chemistry, 6(23), 4296-4298 (2008)
Intramolecular C- H Alkenylation of N-Alkynylindoles: Exo and Endo Selective Cyclization According to the Choice of Metal Catalyst
Shibata, T, et al.
Advanced Synthesis & Catalysis, 359(11), 1849-1853 (2017)
Venukrishnan Komanduri et al.
Journal of the American Chemical Society, 130(38), 12592-12593 (2008-09-02)
Hydrogenation of 2-vinyl azines 1a-1e in the presence of N-arylsulfonyl imines 2a-2l at ambient temperature and pressure employing cationic rhodium catalysts ligated by tri-2-furylphosphine results in regioselective reductive coupling to furnish branched products of imine addition 3a-3v, which embody modest

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