CAS 1208092-27-6 [(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato][1,2,3-n-2-propenyl]iridium(III), min. 97%

Synonyms

MFCD20922908;Krische Ir Catalyst: (S)-SEGPHOS, 4-cyano-3-nitrobenzoate ligated, AldrichCPR;[(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato][1,2,3- -2-propenyl]Ir(III);[(R)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato][1,2,3--2-propenyl]Ir(III);1208092-27-6;

IUPAC Name

4-cyano-3-nitrobenzene-6-ide-1-carboxylic acid;[4-(5-diphenylphosphanyl-1,3-benzodioxol-4-yl)-1,3-benzodioxol-5-yl]-diphenylphosphane;iridium;propane;

Molecular Weight

1034.998g/mol

Molecular Formula

C49H36IrN2O8P2-;

Canonical SMILES

[CH2][CH][CH2].C1OC2=C(O1)C(=C(C=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)C5=C(C=CC6=C5OCO6)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=[C-]C(=CC(=C1C#N)[N+](=O)[O-])C(=O)O.[Ir];

InChI

InChI=1S/C38H28O4P2.C8H3N2O4.C3H5.Ir/c1-5-13-27(14-6-1)43(28-15-7-2-8-16-28)33-23-21-31-37(41-25-39-31)35(33)36-34(24-22-32-38(36)42-26-40-32)44(29-17-9-3-10-18-29)30-19-11-4-12-20-30;9-4-6-2-1-5(8(11)12)3-7(6)10(13)14;1-3-2;/h1-24H,25-26H2;2-3H,(H,11,12);3H,1-2H2;/q;-1;;;

InChI Key

WNUGBSVEKALVKR-UHFFFAOYSA-N;

Complexity

1230

Covalently-Bonded Unit Count

Exact Mass

1035.158g/mol

Formal Charge

-1

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

1035.158g/mol

Rotatable Bond Count

Topological Polar Surface Area

144A^2

Application

The product, (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole [4-cyano-3-nitrobenzenecarboxylato] [1,2,3-n-2-propenyl]iridium(III), with a purity of at least 97%, serves as a versatile catalyst designed to facilitate a range of diastereo- and enantioselective reactions at the carbonyl group. It is specifically used for carbonyl (trimethylsilyl)allylation and (hydroxy)allylation, both vital in forming anti-1,2-diols, as well as (hydroxymethyl)allylation, tert-prenylation, and crotylation from either alcohol or aldehyde oxidation levels. Additionally, it catalyzes double crotylation specifically in 1,3-diols, thus providing significant utility in the enantioselective synthesis of complex organic molecules.

March 11, 2025

Exceptional Catalyst for Research Applications!

I used this product for diastereo- and enantioselective carbonyl reactions in my lab. It performed flawlessly, enhancing reaction efficiency and selectivity for allylations and crotylations. Highly recommend for any synthetic chemistry needs!