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659703

Sigma-Aldrich

(S,S′,R,R′)-TangPhos-rhodium complex

Synonym(s):

(S,S′,R,R′)-TangPhos(cyclooctadiene)rhodium(I) tetrafluoroborate

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About This Item

Empirical Formula (Hill Notation):
C24H44BF4P2Rh
Molecular Weight:
584.26
MDL number:
MFCD07782006
UNSPSC Code:
12352005
PubChem Substance ID:
24884438
NACRES:
NA.22

mp

>300 °C

Quality Level

100

SMILES string

[Rh+].F[B-](F)(F)F.C1CC=CCCC=C1.CC(C)(C)P2CCCC2C3CCCP3C(C)(C)C

InChI

1S/C16H32P2.C8H12.BF4.Rh/c1-15(2,3)17-11-7-9-13(17)14-10-8-12-18(14)16(4,5)6;1-2-4-6-8-7-5-3-1;2-1(3,4)5;/h13-14H,7-12H2,1-6H3;1-2,7-8H,3-6H2;;/q;;-1;+1/b;2-1-,8-7-;;/t13-,14-,17?,18?;;;/m1.../s1

InChI key

MIRRQDFJJORQIW-WTXJZQGQSA-N

General description

(S,S′,R,R′)-TangPhos-rhodium complex is an electron-rich, low molecular weight and rigid P-chiral bisphospholane ligand for transition metal catalyzed asymmetric hydrogenation.

Application

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation
Highly efficient in rhodium-catalyzed hydrogenation of α-dehyroamino acids and α-arylenamides, β-(acylamino)acrylates, itaconic acids, and enol acetates. Also gives outstanding enantioselectivities in asymmetric hydroformylation reactions.

Storage Class Code

13 - Non 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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
01221HD

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Wenjun Tang et al.
Organic letters, 4(23), 4159-4161 (2002-11-09)
The Rh-TangPhos complex is an efficient hydrogenation catalyst for making chiral beta-amino acid derivatives. With the Rh-TangPhos system, high enantioselectivities (up to 99.6%) and turnover numbers have been obtained in the hydrogenation of E/Z isomeric mixtures of both beta-alkyl and
Wenjun Tang et al.
Organic letters, 5(2), 205-207 (2003-01-17)
[reaction: see text] The Rh-TangPhos catalyst has been used for asymmetric hydrogenation of itaconic acid and enol acetate derivatives. A variety of chiral 2-substituted succinic acids and chiral acetates have been obtained in excellent ee values (up to 99% ee).
A chiral 1,2-bisphospholane ligand with a novel structural motif: applications in highly enantioselective Rh-catalyzed hydrogenations.
Wenjun Tang et al.
Angewandte Chemie (International ed. in English), 41(9), 1612-1614 (2002-05-03)
Axtell, A. T. et al.
Organometallics, 25, 5003-5003 (2006)

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