Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles

Wai Wing Chan; Tsz Lung Kwong; Wing Yiu Yu

doi:10.1039/c2ob06985g

Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles

Wai Wing Chan
, Tsz Lung Kwong
, Wing Yiu Yu

The Hong Kong Polytechnic University

Research output: Journal article publication › Journal article › Academic research › peer-review

45 Citations (Scopus)

Abstract

With [Ru(p-cymene)Cl ₂] ₂ as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (k _H/k _D ∼ 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.

Original language	English
Pages (from-to)	3749-3755
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	18
DOIs	https://doi.org/10.1039/c2ob06985g
Publication status	Published - 14 May 2012

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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10.1039/c2ob06985g

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abstract = "With [Ru(p-cymene)Cl 2] 2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92\% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (k H/k D ∼ 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.",

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AU - Chan, Wai Wing

AU - Kwong, Tsz Lung

AU - Yu, Wing Yiu

PY - 2012/5/14

Y1 - 2012/5/14

N2 - With [Ru(p-cymene)Cl 2] 2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (k H/k D ∼ 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.

AB - With [Ru(p-cymene)Cl 2] 2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (k H/k D ∼ 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.

UR - https://www.scopus.com/pages/publications/84859872671

U2 - 10.1039/c2ob06985g

DO - 10.1039/c2ob06985g

M3 - Journal article

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ER -

Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles

Abstract

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