Palladium catalyzed chloroethoxylation of aromatic and heteroaromatic chlorides

An orthogonal functionalization of a chloroethoxy linker

Bálint Petho, Dóra Vangel, János T. Csenki, Márton Zwillinger, Z. Novák

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A novel disconnection based on cross-coupling chemistry was designed to access pharmaceutically relevant aryl-aminoethyl ethers. The developed palladium-catalyzed functionalization of aryl- and heteroaryl chlorides with a sodium tetrakis-(2-chloroethoxy) borate salt is orthogonal to the simple nucleophilic replacement of the chloro function of the ethylene linker. The transformation enables efficient 2-chloroethoxylation in the absence of an additional external base. Subsequent amine substitution of the alkyl halide affords 2-aminoethoxy arenes. The applicability of this method was demonstrated through the synthesis of various aryl- and heteroaryl-alkyl ethers, including the intermediates of marketed drug molecules.

Original languageEnglish
Pages (from-to)4895-4899
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number26
DOIs
Publication statusPublished - Jan 1 2018

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Ethers
Palladium
Chlorides
palladium
ethers
chlorides
Borates
cross coupling
borates
halides
Amines
amines
drugs
ethylene
Substitution reactions
Salts
Sodium
sodium
substitutes
chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Palladium catalyzed chloroethoxylation of aromatic and heteroaromatic chlorides : An orthogonal functionalization of a chloroethoxy linker. / Petho, Bálint; Vangel, Dóra; Csenki, János T.; Zwillinger, Márton; Novák, Z.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 26, 01.01.2018, p. 4895-4899.

Research output: Contribution to journalArticle

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