Novel Rh catalysis in cross-coupling between alkyl halides and arylzinc compounds possessing ortho-COX (X = OR, NMe2, or Ph) groups

Hideki Takahashi, Shinya Inagaki, Yasushi Nishihara, Takanori Shibata, Kentaro Takagi

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Rh-dppf was found to be an efficient catalyst for the cross-coupling between primary alkyl halides bearings-hydrogens and arylzinc compounds possessing carbonyl groups such as ester, amide, or ketone at the ortho position. Various functional groups such as ester, nitrite, or acyloxylate moieties on the halides were tolerated under the catalysis conditions. Arylzinc compounds free of ortho-carbonyl groups reacted well with ethyl 3-iodopropanoate, suggesting that the essential intramolecular interaction between carbonyl groups and Rh promotes the reductive elimination.

Original languageEnglish
Pages (from-to)3037-3040
Number of pages4
JournalOrganic Letters
Volume8
Issue number14
DOIs
Publication statusPublished - 2006 Jul 6
Externally publishedYes

Fingerprint

cross coupling
Catalysis
catalysis
halides
Esters
Bearings (structural)
Carbonyl compounds
Nitrites
Ketones
Amides
Functional groups
esters
Hydrogen
Catalysts
carbonyl compounds
nitrites
ketones
amides
elimination
catalysts

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Novel Rh catalysis in cross-coupling between alkyl halides and arylzinc compounds possessing ortho-COX (X = OR, NMe2, or Ph) groups. / Takahashi, Hideki; Inagaki, Shinya; Nishihara, Yasushi; Shibata, Takanori; Takagi, Kentaro.

In: Organic Letters, Vol. 8, No. 14, 06.07.2006, p. 3037-3040.

Research output: Contribution to journalArticle

Takahashi, Hideki ; Inagaki, Shinya ; Nishihara, Yasushi ; Shibata, Takanori ; Takagi, Kentaro. / Novel Rh catalysis in cross-coupling between alkyl halides and arylzinc compounds possessing ortho-COX (X = OR, NMe2, or Ph) groups. In: Organic Letters. 2006 ; Vol. 8, No. 14. pp. 3037-3040.
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