Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at α-position of tertiary amines

Hirofumi Ueda; Kei Yoshida; Hidetoshi Tokuyama

doi:10.1021/ol5018883

Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at α-position of tertiary amines

Hirofumi Ueda, Kei Yoshida, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

Tohoku University

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

113 Citations (Scopus)

Abstract

The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.

Original language	English
Pages (from-to)	4194-4197
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	16
DOIs	https://doi.org/10.1021/ol5018883
Publication status	Published - 2014 Aug 15

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10.1021/ol5018883

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abstract = "The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.",

author = "Hirofumi Ueda and Kei Yoshida and Hidetoshi Tokuyama",

year = "2014",

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T1 - Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at α-position of tertiary amines

AU - Ueda, Hirofumi

AU - Yoshida, Kei

AU - Tokuyama, Hidetoshi

PY - 2014/8/15

Y1 - 2014/8/15

N2 - The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.

AB - The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.

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Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at α-position of tertiary amines

Abstract

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