CAS 1237588-12-3 MorDalphos - Catalysts / Alfa Chemistry

Synonyms

2-Morpholinophenyldi(1-adamantyl)phosphine; SC11165; bis(1-adamantyl)-(2-morpholin-4-ylphenyl)phosphane; Mor-DalPhos; 4-(2-(Di(adamantan-1-yl)phosphino)phenyl)morpholine; Di(1-adamantyl)-2-morpholinophenylphosphine; ZINC71773616; AK307802;

IUPAC Name

bis(1-adamantyl)-(2-morpholin-4-ylphenyl)phosphane;

Molecular Weight

463.646g/mol

Molecular Formula

C30H42NOP;

Canonical SMILES

C1COCCN1C2=CC=CC=C2P(C34CC5CC(C3)CC(C5)C4)C67CC8CC(C6)CC(C8)C7;

InChI

InChI=1S/C30H42NOP/c1-2-4-28(27(3-1)31-5-7-32-8-6-31)33(29-15-21-9-22(16-29)11-23(10-21)17-29)30-18-24-12-25(19-30)14-26(13-24)20-30/h1-4,21-26H,5-20H2;

InChI Key

CCBRRSUORFMQCZ-UHFFFAOYSA-N;

Storage

2-8°C

Complexity

632

Covalently-Bonded Unit Count

Exact Mass

463.3g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

463.3g/mol

Rotatable Bond Count

Topological Polar Surface Area

12.5A^2

Application

MorDalphos serves as a versatile and efficient green catalytic system designed for facilitating the Buchwald-Hartwig cross-coupling reaction involving aryl bromides or chlorides and a wide array of amines, amides, ureas, and carbamates. Originating from the innovative work of the Stradiotto group, this electron-rich, sterically hindered P,N-based ancillary ligand extends its utility to various chemical transformations. These include the Buchwald-Hartwig Amination reaction, alkyne hydroamination, and the monoarylation of compounds such as ammonia, hydrazine, and acetone. It is particularly effective in Pd-catalyzed cross-coupling of ammonia and hydrazine with a range of sterically challenging aryl chlorides, operating under conditions of low catalyst loading and mild temperatures. Additionally, MorDalphos is applicable in chemoselective arylation processes with diamines and proves effective in both solvent-free and aqueous environments. Moreover, as a P-N ligand, it facilitates gold-catalyzed stereoselective hydroamination of internal alkynes with dialkylamines, producing E-amines, and supports Pd-catalyzed mono-α-arylation of ketones using various substrates, including aryl chlorides, bromides, iodides, mesylates, and tosylates.

February 12, 2025

Outstanding Catalyst for Buchwald-Hartwig Reactions

Mor-DalPhos has been a game-changer in our lab for the Buchwald-Hartwig cross-coupling. Its efficiency with aryl halides and amines under mild conditions is impressive. The low catalyst loading saves resources without compromising results.