Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes

Yoichiro Kuninobu; Mitsumi Nishi; Salprima S. Yudha; Kazuhiko Takai

doi:10.1021/ol800969h

Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes

Yoichiro Kuninobu, Mitsumi Nishi, Salprima S. Yudha, Kazuhiko Takai

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

50 Citations (Scopus)

Abstract

(Chemical Equation Presented) Treatment of β-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO) ₅, and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of β-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.

Original language	English
Pages (from-to)	3009-3011
Number of pages	3
Journal	Organic letters
Volume	10
Issue number	14
DOIs	https://doi.org/10.1021/ol800969h
Publication status	Published - 2008
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol800969h

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abstract = "(Chemical Equation Presented) Treatment of β-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO) 5, and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of β-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.",

author = "Yoichiro Kuninobu and Mitsumi Nishi and Yudha, {Salprima S.} and Kazuhiko Takai",

year = "2008",

doi = "10.1021/ol800969h",

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volume = "10",

pages = "3009--3011",

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T1 - Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes

AU - Kuninobu, Yoichiro

AU - Nishi, Mitsumi

AU - Yudha, Salprima S.

AU - Takai, Kazuhiko

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Treatment of β-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO) 5, and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of β-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.

AB - (Chemical Equation Presented) Treatment of β-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO) 5, and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of β-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.

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JO - Organic letters

JF - Organic letters

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ER -

Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes

Abstract

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