Richard L Heck

US Patent:

39609324, Jun 1, 1976

Filed:

Oct 10, 1974

Appl. No.:

5/513529

Inventors:

Richard F. Heck - Wilmington DE

Assignee:

The University of Delaware - Newark DE

International Classification:

C07C 4500

US Classification:

260479R

Abstract:

Aldehydes are obtained from aryl, vinylic and heterocyclic halides and substituted derivatives thereof, a tertiary amine, carbon monoxide and hydrogen at from about 50. degree. -175. degree. C under from about one to 200 atmospheres pressure and with PdX. sub. 2 [P(C. sub. 6 H. sub. 5). sub. 3 ]. sub. 1 or 2 as a catalyst where X is acetate or a halogen. The ratios of carbon monoxide to hydrogen are not critical but the most favorable reactions are usually obtained with ratio from about 0. 1 to about 10. A typical example is the conversion of p-bromoanisole to anisaldehyde in 84% yield at 150. degree. C in 18 hrs. at 1000 psig. of 1:1 CO to H. sub. 2 with one mole percent of PdBr. sub. 2 [P(C. sub. 6 H. sub. 5). sub. 3 ]. sub. 2 as catalyst and with tri-n-butylamine as the tertiary amine.

US Patent:

41285549, Dec 5, 1978

Filed:

Mar 10, 1977

Appl. No.:

5/776289

Inventors:

Richard F. Heck - Wilmington DE

Assignee:

University of Delaware - Newark DE

International Classification:

C07D21356
C07C10375

US Classification:

546317

Abstract:

Carboxylic acid amides are obtained from aryl, heterocyclic, and vinylic halides and substituted derivates thereof, by reacting same with a primary or secondary amine and carbon monoxide, in the presence of a palladium catalyst and if necessry a tertiary amine at about 20. degree. -150. degree. C and from at least a half atmosphere pressure.

US Patent:

39883582, Oct 26, 1976

Filed:

May 10, 1974

Appl. No.:

5/468762

Inventors:

Richard F. Heck - Wilmington DE

Assignee:

The University of Delaware - Newark DE

International Classification:

C07C 6736
C07C 6954
C07C 6978
C07C12152

US Classification:

260465D

Abstract:

Carboxylic acid esters or amides are obtained from aryl, heterocyclic, vinylic, ethynylic, and benzylic halides and substituted derivates thereof, by reacting same with an alcohol or primary or secondary amine and carbon monoxide, in the presence of a palladium catalyst and if necessary a tertiary amine at about 20. degree. -150. degree. C and from about a half to about 100 atmospheres pressure. A typical example is the conversion of bromobenzene into n-butyl benzoate at 100. degree. C and one atmosphere of carbon monoxide in the presence of tri-n-butyl-amine and a catalytic amount of PdBr. sub. 2 [P(C. sub. 6 H. sub. 5). sub. 3 ]. sub. 2.

US Patent:

41751876, Nov 20, 1979

Filed:

Oct 24, 1978

Appl. No.:

5/954184

Inventors:

Richard F. Heck - Wilmington DE

Assignee:

University of Delaware - Newark DE

International Classification:

C07D29502

US Classification:

544170

Abstract:

Tertiary allylic amines are obtained from vinylic halides and olefins, and substituted derivatives thereof, by reacting said halide with a mono-, di-, or tri-substituted olefin and an unhindered basic secondary amine in the presence of a palladium catalyst.