Direct anti-markovnikov addition of acids to alkenes

Patent metadata

Field	Value
Publication number	US-9365530-B2
Application number	US-201314397603-A
Country	US
Kind code	B2
Filing date	May 6, 2013
Priority date	May 7, 2012
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

A method of making an anti-Markovnikov addition product is carried out by reacting an acid with an alkene or alkyne in a dual catalyst reaction system to the exclusion of oxygen to produce said anti-Markovnikov addition product; the dual catalyst reaction system comprising a single electron oxidation catalyst in combination with a hydrogen atom donor catalyst. Compositions useful for carrying out such methods are also described.

First claim

That which is claimed is:

1. A method of making an anti-Markovnikov addition product, comprising:
reacting an aliphatic organic acid with an alkene in a dual catalyst reaction system to the exclusion of oxygen to produce said anti-Markovnikov addition product;
said dual catalyst reaction system comprising a single electron oxidation catalyst in combination with a hydrogen atom donor catalyst,
wherein said single electron oxidation catalyst has the structure:

and wherein said hydrogen atom donor catalyst has the structure:

2. The method of claim 1 , wherein said reacting is an intramolecular hydroalkoxylation reaction.

3. The method of claim 1 , wherein said reacting is an intramolecular hydrolactonization reaction.

4. The method of claim 1 , wherein said reacting is an intermolecular hydroacetoxylation reaction.

5. The method of claim 1 , wherein said reacting is an anti-Markovnikov polymerization reaction where the acid and alkene group are contained within the same monomeric unit or are contained on separate monomeric units.

Assignees

• Univ North Carolina

Inventors

• Nicewicz David A
• Hamilton David S
• Perkowski Andrew J

Classifications

• C07D313/04

  not condensed with other rings · CPC title

• B01J31/0235

  Nitrogen containing compounds · CPC title

• B01J35/004

  Operations & Transport · mapped topic

• B01J31/0244

  with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine · CPC title

• B01J2231/324

  Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions · CPC title