Rhodium-catalyzed anti-markovnikov addition of secondary amines to arylacetylenes at room temperature

Kazunori Sakai; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/ol201453h

Rhodium-catalyzed anti-markovnikov addition of secondary amines to arylacetylenes at room temperature

Kazunori Sakai, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

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

40 Citations (Scopus)

Abstract

An efficient method for synthesis of E-enamines by the anti-Markovnikov addition of secondary amines to terminal alkynes is described. The reaction of a variety of aryl- and heteroarylacetylenes proceeded at room temperature using a combination of a 8-quinolinolato rhodium complex and P(p-MeOC₆H ₄)₃ as a catalyst. The products were obtained as enamines by simple bulb-to-bulb distillation.

Original language	English
Pages (from-to)	3928-3931
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	15
DOIs	https://doi.org/10.1021/ol201453h
Publication status	Published - 2011 Aug 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An efficient method for synthesis of E-enamines by the anti-Markovnikov addition of secondary amines to terminal alkynes is described. The reaction of a variety of aryl- and heteroarylacetylenes proceeded at room temperature using a combination of a 8-quinolinolato rhodium complex and P(p-MeOC6H 4)3 as a catalyst. The products were obtained as enamines by simple bulb-to-bulb distillation.",

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AU - Sakai, Kazunori

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

PY - 2011/8/5

Y1 - 2011/8/5

N2 - An efficient method for synthesis of E-enamines by the anti-Markovnikov addition of secondary amines to terminal alkynes is described. The reaction of a variety of aryl- and heteroarylacetylenes proceeded at room temperature using a combination of a 8-quinolinolato rhodium complex and P(p-MeOC6H 4)3 as a catalyst. The products were obtained as enamines by simple bulb-to-bulb distillation.

AB - An efficient method for synthesis of E-enamines by the anti-Markovnikov addition of secondary amines to terminal alkynes is described. The reaction of a variety of aryl- and heteroarylacetylenes proceeded at room temperature using a combination of a 8-quinolinolato rhodium complex and P(p-MeOC6H 4)3 as a catalyst. The products were obtained as enamines by simple bulb-to-bulb distillation.

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Rhodium-catalyzed anti-markovnikov addition of secondary amines to arylacetylenes at room temperature

Abstract

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