Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage

Ze Kun Yang; Dong Yu Wang; Hiroki Minami; Hiroyuki Ogawa; Takashi Ozaki; Tatsuo Saito; Kazunori Miyamoto; Chao Wang; Masanobu Uchiyama

doi:10.1002/chem.201603436

Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage

Ze Kun Yang, Dong Yu Wang, Hiroki Minami, Hiroyuki Ogawa, Takashi Ozaki, Tatsuo Saito, Kazunori Miyamoto, Chao Wang, Masanobu Uchiyama

研究成果: Article › 査読

55 被引用数 (Scopus)

抄録

Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C−O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)₂] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C−N bond cleavage in the presence of a [Pd(PPh₃)₂Cl₂] catalyst. These methods enable selective sequential functionalizations of arenes having both C−N and C−O bonds in one pot.

本文言語	English
ページ（範囲）	15693-15699
ページ数	7
ジャーナル	Chemistry - A European Journal
巻	22
号	44
DOI	https://doi.org/10.1002/chem.201603436
出版ステータス	Published - 2016 10月 24
外部発表	はい

ASJC Scopus subject areas

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有機化学

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title = "Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage",

abstract = "Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C−O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)2] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C−N bond cleavage in the presence of a [Pd(PPh3)2Cl2] catalyst. These methods enable selective sequential functionalizations of arenes having both C−N and C−O bonds in one pot.",

keywords = "ammonium salt, cross-coupling, ether, organolithium, transition metal catalyst",

author = "Yang, {Ze Kun} and Wang, {Dong Yu} and Hiroki Minami and Hiroyuki Ogawa and Takashi Ozaki and Tatsuo Saito and Kazunori Miyamoto and Chao Wang and Masanobu Uchiyama",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage

AU - Yang, Ze Kun

AU - Wang, Dong Yu

AU - Minami, Hiroki

AU - Ogawa, Hiroyuki

AU - Ozaki, Takashi

AU - Saito, Tatsuo

AU - Miyamoto, Kazunori

AU - Wang, Chao

AU - Uchiyama, Masanobu

PY - 2016/10/24

Y1 - 2016/10/24

N2 - Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C−O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)2] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C−N bond cleavage in the presence of a [Pd(PPh3)2Cl2] catalyst. These methods enable selective sequential functionalizations of arenes having both C−N and C−O bonds in one pot.

AB - Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C−O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)2] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C−N bond cleavage in the presence of a [Pd(PPh3)2Cl2] catalyst. These methods enable selective sequential functionalizations of arenes having both C−N and C−O bonds in one pot.

KW - ammonium salt

KW - cross-coupling

KW - ether

KW - organolithium

KW - transition metal catalyst

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Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage

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