Process for the palladium catalyzed coupling of a diazonium salt

Details Process for the palladium catalyzed coupling of a diazonium salt Process for the palladium catalyzed coupling of a diazonium salt

1992-01-22

1993-12-28

Higel, Floyd D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

534565, 562495, C07C 5742, C07C 5744, C07C 69618

Patent

active

052741710

ABSTRACT:
A "one-pot" process for the palladium catalyzed coupling of a diazonium salt with an olefinic bond, in the aqueous medium in which the diazonium salt is made, by employing a carboxylic acid as a solvent. Arylacrylic acids and their esters, e.g. the cinnamates, can be produced at low catalyst concentration without first isolating the diazonium salt. The process is applied to the synthesis of 2-ethylhexyl p-methoxycinnamate.

REFERENCES:
patent: 4145362 (1979-03-01), Brepoels et al.
patent: 4970332 (1990-11-01), Caskey
K. Shank, "Preparation of Diazonium Groups" in The Chemistry of Diazonium and Diazo Groups, Part 2, S. Patei, Ed., John Wiley, N.Y. (1978) pp. 645-657.
R. Heck, "Palladium Reagents In Organic Synthesis", (1985), Academic Press, N.Y., pp. 287-290, 446.
K. Kikukawa et al. IV, Tetrahedron, 37 (1981), pp. 31--36.
K. Kikukawa et al., I Chem. Let. (1977), pp. 159-162.
K. Kikukaw et al., II Bull. Chem. Soc. Jap., 52 (1979), pp. 2609-2610.
K. Kikukawa et al., III Chem. Let. (1980), pp. 551-552.
K. Kikukawa et al., IV J. Org. Chem. 46 (1981), pp. 4885-4888.

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