2:1 versus 1:1 Coupling of Alkylacetylenes with Secondary Amines: Selectivity Switching in 8-Quinolinolato Rhodium Catalysis

Yoshihiko Morimoto; Moe Hamada; Shotaro Takano; Katsufumi Mochizuki; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/acs.orglett.1c00094

2:1 versus 1:1 Coupling of Alkylacetylenes with Secondary Amines: Selectivity Switching in 8-Quinolinolato Rhodium Catalysis

Yoshihiko Morimoto, Moe Hamada, Shotaro Takano, Katsufumi Mochizuki, Takuya Kochi, Fumitoshi Kakiuchi

化学科

研究成果: Article › 査読

4 被引用数 (Scopus)

抄録

Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while one-pot coupling/hydrolysis gave enones as products. In toluene, anti-Markovnikov hydroamination occurred under relatively mild conditions to give 1:1 coupling products.

本文言語	English
ページ（範囲）	3803-3808
ページ数	6
ジャーナル	Organic Letters
巻	23
号	10
DOI	https://doi.org/10.1021/acs.orglett.1c00094
出版ステータス	Published - 2021 5月 21

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/acs.orglett.1c00094

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引用スタイル

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abstract = "Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while one-pot coupling/hydrolysis gave enones as products. In toluene, anti-Markovnikov hydroamination occurred under relatively mild conditions to give 1:1 coupling products. ",

author = "Yoshihiko Morimoto and Moe Hamada and Shotaro Takano and Katsufumi Mochizuki and Takuya Kochi and Fumitoshi Kakiuchi",

note = "Funding Information: F.K. acknowledges financial support, in part, by the Promotion of Science (JSPS) KAKENHI Grant No. JP15H05839 in Middle Molecular Strategy, Japan. Y.M. is also grateful for support by the Research Grant of Keio Leading-edge Laboratory of Science & Technology and Research Grant of Keio Research Development and Sponsored Projects, Faculty of Science & Technology. Publisher Copyright: {\textcopyright} ",

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T2 - Selectivity Switching in 8-Quinolinolato Rhodium Catalysis

AU - Morimoto, Yoshihiko

AU - Hamada, Moe

AU - Takano, Shotaro

AU - Mochizuki, Katsufumi

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

N1 - Funding Information: F.K. acknowledges financial support, in part, by the Promotion of Science (JSPS) KAKENHI Grant No. JP15H05839 in Middle Molecular Strategy, Japan. Y.M. is also grateful for support by the Research Grant of Keio Leading-edge Laboratory of Science & Technology and Research Grant of Keio Research Development and Sponsored Projects, Faculty of Science & Technology. Publisher Copyright: ©

PY - 2021/5/21

Y1 - 2021/5/21

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AB - Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while one-pot coupling/hydrolysis gave enones as products. In toluene, anti-Markovnikov hydroamination occurred under relatively mild conditions to give 1:1 coupling products.

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