Cyclization of 5-alkynones with chromium alkylidene equivalents generated: In situ from gem -dichromiomethanes

Masahito Murai; Ryuji Taniguchi; Takashi Kurogi; Moritani Shunsuke; Kazuhiko Takai

doi:10.1039/d0cc03986a

Cyclization of 5-alkynones with chromium alkylidene equivalents generated: In situ from gem -dichromiomethanes

Masahito Murai, Ryuji Taniguchi, Takashi Kurogi, Moritani Shunsuke, Kazuhiko Takai

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

A rare example of cyclization with 5-alkynones, which possess non-polar alkynyl and less electrophilic polar keto carbonyl groups, was demonstrated. The key to promoting carbene/alkyne metathesis followed by alkylidenation with pendant CO double bonds was the Schrock-type nucleophilic reactivity of the generated chromium carbene equivalents from readily available diiodomethanes and CrCl2 by simple heating.

Original language	English
Pages (from-to)	9711-9714
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	67
DOIs	https://doi.org/10.1039/d0cc03986a
Publication status	Published - Aug 28 2020

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "A rare example of cyclization with 5-alkynones, which possess non-polar alkynyl and less electrophilic polar keto carbonyl groups, was demonstrated. The key to promoting carbene/alkyne metathesis followed by alkylidenation with pendant CO double bonds was the Schrock-type nucleophilic reactivity of the generated chromium carbene equivalents from readily available diiodomethanes and CrCl2 by simple heating.",

author = "Masahito Murai and Ryuji Taniguchi and Takashi Kurogi and Moritani Shunsuke and Kazuhiko Takai",

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T1 - Cyclization of 5-alkynones with chromium alkylidene equivalents generated

T2 - In situ from gem -dichromiomethanes

AU - Murai, Masahito

AU - Taniguchi, Ryuji

AU - Kurogi, Takashi

AU - Shunsuke, Moritani

AU - Takai, Kazuhiko

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research (A) 18H03911 from MEXT, Japan. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2020/8/28

Y1 - 2020/8/28

N2 - A rare example of cyclization with 5-alkynones, which possess non-polar alkynyl and less electrophilic polar keto carbonyl groups, was demonstrated. The key to promoting carbene/alkyne metathesis followed by alkylidenation with pendant CO double bonds was the Schrock-type nucleophilic reactivity of the generated chromium carbene equivalents from readily available diiodomethanes and CrCl2 by simple heating.

AB - A rare example of cyclization with 5-alkynones, which possess non-polar alkynyl and less electrophilic polar keto carbonyl groups, was demonstrated. The key to promoting carbene/alkyne metathesis followed by alkylidenation with pendant CO double bonds was the Schrock-type nucleophilic reactivity of the generated chromium carbene equivalents from readily available diiodomethanes and CrCl2 by simple heating.

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JO - Chemical Communications

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Cyclization of 5-alkynones with chromium alkylidene equivalents generated: In situ from gem -dichromiomethanes

Abstract

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