- Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids
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A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.
- Deng, Guobo,Liang, Yun,Luo, Xiai,Yang, Xiumei,Yang, Yuan,Yang, Yuzhong,Zhou, Liwei
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supporting information
p. 1223 - 1230
(2020/04/15)
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- A palladium-catalyzed multi-component annulation approach towards the synthesis of phenanthrenes
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An efficient palladium-catalyzed three-component cascade reaction has been developed for the facile construction of phenanthrene frameworks. The transformation is driven by a controlled reaction sequence of Suzuki-Miyaura coupling followed by the insertion of alkynes, and finally, annulation to yield phenanthrene derivatives via C-H activation. This methodology is able to accommodate a variety of substrates and affords the anticipated products in good to excellent yields.
- Song, Juan,Wang, Songjiang,Sun, Haisen,Fan, Yuxuan,Xiao, Kang,Qian, Yan
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supporting information
p. 3328 - 3332
(2019/04/01)
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- Palladium-Catalyzed Regioselective Aromatic Extension of Internal Alkynes through a Norbornene-Controlled Reaction Sequence
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A regioselective aromatic π-extension reaction of internal alkynes is reported. The proposed method employs three easily available components, namely aryl halides, 2-haloarylcarboxylic acids, and disubstituted acetylenes. The transformation is driven by a controlled reaction sequence of C?H activation, decarboxylation, and annulation to give poly(hetero)aromatic compounds in a site-selective fashion. Unlike in previously reported palladium-catalyzed three-component annulations, alkyne carbopalladation is the last step of this tandem reaction.
- Zhao, Qingyang,Fu, Wai Chung,Kwong, Fuk Yee
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supporting information
p. 3381 - 3385
(2018/02/27)
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- Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation
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A novel protocol for palladium-catalyzed intermolecular formal [4 + 2] annulation of 2-phenylbenzoic acids with alkynes is described. Acridine is shown to be essential for the high reaction efficiency. Phenanthrene derivatives are formed in moderate to good yields without coupling (pseudo)halides or organometallic species.
- Wang, Congyang,Rakshit, Souvik,Glorius, Frank
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supporting information; experimental part
p. 14006 - 14008
(2010/12/24)
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