Tri-(adamantyl) phosphines and applications thereof

Patent metadata

Field	Value
Publication number	US-12539508-B2
Application number	US-202318367813-A
Country	US
Kind code	B2
Filing date	Sep 13, 2023
Priority date	Oct 29, 2015
Publication date	Feb 3, 2026
Grant date	Feb 3, 2026

Abstract

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd 3 ) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd 3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

First claim

The invention claimed is:

1 . A transition metal complex of the formula:

wherein PAd 3 is tri(1-adamantyl)phosphine and X is selected from the group consisting of F, Cl, Br, I, OAc, substituted benzoate, TFA, OTs, OMs, and OTf, and R is selected from the group consisting of alkyl, aryl, heteroaryl, CO, cyano, hydroxyl, η 3 -allyl, η 3 -crotyl, η 3 -cinnamyl and η 3 -indenyl, and M is a transition metal selected from Group VIIIA, IB or IIB of the Periodic Table, wherein the transition metal complex is in powder form.

2 . The transition metal complex of claim 1 , wherein Mis a noble metal.

3 . The transition metal complex of claim 2 , wherein M is selected from the group consisting of palladium, rhodium, silver and gold.

4 . The transition metal complex of claim 3 , wherein Mis palladium.

5 . The transition metal complex of claim 1 , wherein R is aryl.

6 . The transition metal complex of claim 5 , wherein the aryl is selected from the group consisting of phenyl, substituted phenyl,

7 . The transition metal complex of claim 1 , wherein the transition metal complex comprises {2-[(acetyl-κO)amino)phenyl-κC](tri-1-adamantylphosphine)palladium} + .

8 . The transition metal complex of claim 1 , wherein the transition metal complex comprises Pd(PAd 3 )(Ph)(κ 2 -OAc).

Assignees

• Univ Princeton

Inventors

• Carrow Brad P
• Chen Liye

Classifications

• C07F3/00

  Compounds containing elements of Groups 2 or 12 of the Periodic Table · CPC title

• C07F1/00

  Compounds containing elements of Groups 1 or 11 of the Periodic Table · CPC title

• B01J2540/442

  Amide groups or imidato groups (R-C=NR(OR)) · CPC title

• B01J2531/824

  Palladium · CPC title

• B01J2531/822

  Rhodium · CPC title