Rh-Catalyzed Direct Carboxylation of Alkenyl C−H Bonds of Alkenylpyrazoles

Takanobu Saitou; Yushu Jin; Kotaro Isobe; Takuya Suga; Jun Takaya; Nobuharu Iwasawa

doi:10.1002/asia.202000476

Rh-Catalyzed Direct Carboxylation of Alkenyl C−H Bonds of Alkenylpyrazoles

Takanobu Saitou, Yushu Jin, Kotaro Isobe, Takuya Suga, Jun Takaya, Nobuharu Iwasawa

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研究成果: Article › 査読

13 被引用数 (Scopus)

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The Rh-catalyzed direct carboxylation of alkenyl C−H bonds was achieved by using pyrazole as a removable directing group. In the presence of 5 mol% RhCl₃ ⋅ 3H₂O, 6 mol% P(Mes)₃, and 2 equiv. of AlMe₂(OMe), the alkenyl C−H bond of various alkenylpyrazoles was directly carboxylated in good yields under CO₂ atmosphere. Furthermore, several useful transformations of the pyrazole moiety of the product were achieved to afford synthetically useful carboxylic acid derivatives in good yields.

本文言語	English
ページ（範囲）	1941-1944
ページ数	4
ジャーナル	Chemistry - An Asian Journal
巻	15
号	13
DOI	https://doi.org/10.1002/asia.202000476
出版ステータス	Published - 1 7月 2020

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title = "Rh-Catalyzed Direct Carboxylation of Alkenyl C−H Bonds of Alkenylpyrazoles",

abstract = "The Rh-catalyzed direct carboxylation of alkenyl C−H bonds was achieved by using pyrazole as a removable directing group. In the presence of 5 mol% RhCl3 ⋅ 3H2O, 6 mol% P(Mes)3, and 2 equiv. of AlMe2(OMe), the alkenyl C−H bond of various alkenylpyrazoles was directly carboxylated in good yields under CO2 atmosphere. Furthermore, several useful transformations of the pyrazole moiety of the product were achieved to afford synthetically useful carboxylic acid derivatives in good yields.",

keywords = "Rh(I) catalyst, alkenyl C–H activation, carboxylation, pyrazole",

author = "Takanobu Saitou and Yushu Jin and Kotaro Isobe and Takuya Suga and Jun Takaya and Nobuharu Iwasawa",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Rh-Catalyzed Direct Carboxylation of Alkenyl C−H Bonds of Alkenylpyrazoles

AU - Saitou, Takanobu

AU - Jin, Yushu

AU - Isobe, Kotaro

AU - Suga, Takuya

AU - Takaya, Jun

AU - Iwasawa, Nobuharu

PY - 2020/7/1

Y1 - 2020/7/1

N2 - The Rh-catalyzed direct carboxylation of alkenyl C−H bonds was achieved by using pyrazole as a removable directing group. In the presence of 5 mol% RhCl3 ⋅ 3H2O, 6 mol% P(Mes)3, and 2 equiv. of AlMe2(OMe), the alkenyl C−H bond of various alkenylpyrazoles was directly carboxylated in good yields under CO2 atmosphere. Furthermore, several useful transformations of the pyrazole moiety of the product were achieved to afford synthetically useful carboxylic acid derivatives in good yields.

AB - The Rh-catalyzed direct carboxylation of alkenyl C−H bonds was achieved by using pyrazole as a removable directing group. In the presence of 5 mol% RhCl3 ⋅ 3H2O, 6 mol% P(Mes)3, and 2 equiv. of AlMe2(OMe), the alkenyl C−H bond of various alkenylpyrazoles was directly carboxylated in good yields under CO2 atmosphere. Furthermore, several useful transformations of the pyrazole moiety of the product were achieved to afford synthetically useful carboxylic acid derivatives in good yields.

KW - Rh(I) catalyst

KW - alkenyl C–H activation

KW - carboxylation

KW - pyrazole

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SN - 1861-4728

VL - 15

SP - 1941

EP - 1944

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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ER -

Rh-Catalyzed Direct Carboxylation of Alkenyl C−H Bonds of Alkenylpyrazoles

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