- Nickel-Catalyzed Kumada Coupling of Boc-Activated Aromatic Amines via Nondirected Selective Aryl C-N Bond Cleavage
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A nickel-catalyzed Kumada coupling of aniline derivatives was developed by selective cleavage of aryl C-N bonds under mild reaction conditions. Without preinstallation of an ortho directing group on anilines, the cross-coupling reactions of Boc-protected aromatic amines with aryl Grignard reagents afforded unsymmetric biaryls. Mechanistic studies by DFT calculations revealed that the nickel-mediated C-N bond cleavage is the rate-limiting step.
- Zhang, Zheng-Bing,Ji, Chong-Lei,Yang, Ce,Chen, Jie,Hong, Xin,Xia, Ji-Bao
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supporting information
p. 1226 - 1231
(2019/02/14)
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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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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.
- Yang, Ze-Kun,Wang, Dong-Yu,Minami, Hiroki,Ogawa, Hiroyuki,Ozaki, Takashi,Saito, Tatsuo,Miyamoto, Kazunori,Wang, Chao,Uchiyama, Masanobu
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supporting information
p. 15693 - 15699
(2016/10/25)
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- Aryl ether as a Negishi coupling partner: An approach for constructing C-C bonds under mild conditions
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An etheric Negishi coupling: The first cross-coupling reaction between aryl alkyl ethers and dianion-type zincate reagents to afford biaryl compounds through selective cleavage of the etheric C(sp2)-O bond was developed. Dianion-type zincates showed excellent reactivity toward the aromatic ethers under mild conditions, with good functional group compatibility (see scheme). Copyright
- Wang, Chao,Ozaki, Takashi,Takita, Ryo,Uchiyama, Masanobu
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supporting information; experimental part
p. 3482 - 3485
(2012/05/04)
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- Direct application of phenolic salts to nickel-catalyzed cross-coupling reactions with aryl grignard reagents
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(Figure Presented) You're nickel'd pal! The first successful coupling reaction with the direct application of naphtholates as electrophiles (see scheme, X = halide) improves both the step economy and atom economy of cross-coupling reactions whilst decreas
- Yu, Da-Gang,Li, Bi-Jie,Zheng, Shu-Fang,Guan, Bing-Tao,Wang, Bi-Qing,Shi, Zhang-Jie
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supporting information; experimental part
p. 4566 - 4570
(2010/09/10)
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