Markovnikov-selective palladium catalyst for carbonylation of alkynes with heteroarenes

Patent metadata

Field	Value
Publication number	US-10589263-B2
Application number	US-201816014115-A
Country	US
Kind code	B2
Filing date	Jun 21, 2018
Priority date	Jun 29, 2017
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

The carbonylation catalyst is suited for the preparation of a branched heteroarene-keto product from an alkyne substrate, CO and heterocycle in high yields with low amounts of the linear product.

First claim

The invention claimed is:

1. Compound having the structure (1):

2. A process for Markovnikov-selective carbonylation of an alkyne in whose molecule there is one hydrogen atom bonded to a triply bonded carbon atom to form a heteroarene-keto product comprising the following process steps to form a reaction mixture:
a) initially charging the alkyne,
b) adding a compound according to claim 1 and a substance including Pd,
c) feeding N-methylpyrrole and CO,
d) heating the reaction mixture to react the alkyne with CO and N-methylpyrrole to form the heteroarene-keto product.

Assignees

• Evonik Degussa Gmbh

Inventors

• Li Haoquan
• Liu Jie
• Jackstell Ralf
• Beller Matthias
• Franke Robert

Classifications

• C07D207/333

  Radicals substituted by oxygen or sulfur atoms · CPC title

• B01J2540/40

  Non-coordinating groups comprising nitrogen · CPC title

• C07F15/006

  Palladium compounds · CPC title

• B01J31/2234

  Beta-dicarbonyl ligands, e.g. acetylacetonates · CPC title

• B01J31/24 Primary

  Phosphines {, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands} · CPC title