Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N -sulfonyl-1,2,3-triazoles

Tomoya Miura; Tsuneaki Biyajima; Tetsuji Fujii; Masahiro Murakami

doi:10.1021/ja2104203

Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N -sulfonyl-1,2,3-triazoles

Tomoya Miura, Tsuneaki Biyajima, Tetsuji Fujii, Masahiro Murakami

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

205 Citations (Scopus)

Abstract

N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

Original language	English
Pages (from-to)	194-196
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	134
Issue number	1
DOIs	https://doi.org/10.1021/ja2104203
Publication status	Published - Jan 11 2012
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.",

author = "Tomoya Miura and Tsuneaki Biyajima and Tetsuji Fujii and Masahiro Murakami",

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AU - Fujii, Tetsuji

AU - Murakami, Masahiro

PY - 2012/1/11

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AB - N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

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Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N -sulfonyl-1,2,3-triazoles

Abstract

ASJC Scopus subject areas

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