Cross‐Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage |
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| Authors: | Ze‐Kun Yang Dong‐Yu Wang Hiroki Minami Hiroyuki Ogawa Takashi Ozaki Dr. Tatsuo Saito Dr. Kazunori Miyamoto Dr. Chao Wang Prof. Dr. Masanobu Uchiyama |
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| Affiliation: | 1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo-to, Japan;2. Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, RIKEN Elements Chemistry Laboratory, Saitama-ken, Japan |
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| 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. |
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| Keywords: | ammonium salt cross-coupling ether organolithium transition metal catalyst |
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