US 2026/0295571 A1 · DESIGN AND SYNTHESIS OF ELECTRON-RICH PHOSPHINE LIGANDS FOR SELECTIVE, SUSTAINABLE CROSS-COUPLING REACTIONS

Abstract

A family of highly electron rich monophosphine compounds is described. The monophosphines can be prepared from inexpensive materials in one or two steps. The monophosphines can be used as ligands in transition metal or organometallic catalysis for cross-couplings and other new bond-forming reactions. A pre-catalyst palladium complex containing an exemplary monophosphine compound, i.e., AshPhos, and its use in palladium-catalyzed Buchwald-Hartwig amination reactions are described. The coupling partners for the reactions include five- and six-membered (hetero)aryl halides and cyclic secondary or bulky amines. Use of the pre-catalyst palladium complex in catalyzing cyanide ion-free cyanation reactions is also described.

Claims28

Dependent claims

A compound having a structure of Formula (I):

wherein:
R1 and R3 are independently selected from C1-C6 alkyl, C1-C6 alkoxy, and N(R6)2;
R2 and R4 are independently selected from H, C1-C6 alkyl, C1-C6 alkoxy, benzyl, substituted benzyl, and N(R6)2;
or wherein R1 and R2 together and/or R3 and R4 together are —CH═CH—CH═CH— or —O—(C(R7)2)n—O—, wherein n is 1 or 2 and each R7 is H or halo, optionally H or F;
R5 is selected from the group consisting of alkyl, cycloalkyl, aryl, 2-pyridyl, and N(R6)2;
and
each R6 is independently C1-C6 alkyl.

4 more elements

Dependencies are inferred from the claim text.

Facts

Application

19/570,853Filed 18 Mar 2026

Priority

18 Mar 2025

Published

1 Oct 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

B01J 31/2447
Comprising condensed ring systems: and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
B01J 37/04
Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts: mixing
B01J 37/08
Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts: heat treatment
C07F 9/505
Organo-phosphines: preparation; Separation; Purification; Stabilisation

Design and synthesis of electron-rich phosphine ligands for selective, sustainable cross-coupling reactions

Life of this patent

Design and synthesis of electron-rich phosphine ligands for selective, sustainable cross-coupling reactions

Life of this patent

Abstract

Claims28