Organochromium Reagents for Highly Selective Carbon-Carbon Bond Formation

Kazuhiko Takai, Kiitiro Utimoto

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Although the reducing power of chromium (II) salts is not so strong as such metals like lithium, magnesium, and zinc, active organic halides are reduced by chromium (II) to give the corresponding organochromium reagents. We describe here a new entry of the organochromium reagents, which add to aldehydes with unique selectivities, especially chemoselective addition to aldehydes in the presence of ketones. The following topics are included : (1) γ-Alkoxy-substituted allylchromium reagents, produced by reduction of acrolein dialkyl acetals with CrCl2, add to aldehydes in a erythro-selective manner. (2) Alkynyl halides and α-chloro sulfides are reduced by CrCl2 to afford alkynyl and α-thioalkylchromium reagents, respectively. (3) Under nickel catalysis, alkenyl halides (triflates) are reduced by CrCl2 to produce alkenylchromium reagents. (4) Selective synthesis of E-olefins from aldehydes are achieved by using geminal dichromium reagents derived by chromium (II)-reduction of geminal dihalo compounds such as RCHI2, Me3SiCHBr2, and CHX3.

Original languageEnglish
Pages (from-to)66-77
Number of pages12
JournalJournal of Synthetic Organic Chemistry, Japan
Volume46
Issue number1
DOIs
Publication statusPublished - 1988
Externally publishedYes

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Carbon
Aldehydes
Chromium
Acrolein
Acetals
Alkenes
Sulfides
Nickel
Ketones
Lithium
Magnesium
Catalysis
Zinc
Salts
Metals

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Organochromium Reagents for Highly Selective Carbon-Carbon Bond Formation. / Takai, Kazuhiko; Utimoto, Kiitiro.

In: Journal of Synthetic Organic Chemistry, Japan, Vol. 46, No. 1, 1988, p. 66-77.

Research output: Contribution to journalArticle

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