CAS 1070663-78-3 BrettPhos - Catalysts / Alfa Chemistry

Synonyms

C35H53O2P; dicyclohexyl-(2',4',6'-triisopropyl-3,6-dimethoxy-biphenyl-2-yl)-phosphane; BrettPhos; 2-(Dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl; ZINC43220891; ST24046493; 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISOPROPYL-3,6-DIMETHOXYBIPHENYL; AS-19342; 2-(Dicyclohexylphosphino)3,6-dimethoxy-2 inverted exclamation marka,4 inverted exclamation marka,6 inverted exclamation marka-triisopropyl-1,1 inverted exclamation marka-biphenyl; 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl;

IUPAC Name

dicyclohexyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;

Molecular Weight

536.781g/mol

Molecular Formula

C35H53O2P;

Canonical SMILES

CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C;

InChI

InChI=1S/C35H53O2P/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28/h19-25,27-28H,9-18H2,1-8H3;

InChI Key

WDVGNXKCFBOKDF-UHFFFAOYSA-N;

Complexity

643

Covalently-Bonded Unit Count

Exact Mass

536.378g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

536.378g/mol

Rotatable Bond Count

Topological Polar Surface Area

18.5A^2

UNII

4NJ39STQ41

Application

BrettPhos serves as a versatile ligand in a range of catalytic applications, most notably in palladium-catalyzed processes. It facilitates the Suzuki-Miyaura coupling of tosylates and mesylates, and it is particularly effective in cross-coupling reactions involving primary arylamines and aryl iodides, even at low catalyst loadings. Additionally, BrettPhos is instrumental in palladium-catalyzed trifluoromethylation of aryl chlorides and in forming aryl-SCF3 compounds from aryl bromides. This ligand also supports nickel-catalyzed cross-coupling of styrenyl epoxides with boronic acids and enables the intramolecular CH difluoroalkylation. Its utility in coupling reactions with electron-deficient anilines emphasizes BrettPhos's essential role in modern chemical synthesis as part of the Buchwald phosphine ligands repertoire.

March 25, 2025

Efficient Catalyst for Cross-Coupling Reactions

BrettPhos is invaluable for facilitating Suzuki-Miyaura and various palladium-catalyzed coupling reactions. Its low catalyst loading and versatility improved the efficiency of my research significantly. Highly recommend for industrial and scientific applications.