Palladium-catalysed construction of butafulvenes

被引：0
作者：
Xin Huang
Bing-Zhi Chen
Pengbin Li
Ding-Wei Ji
Jinxian Liu
Hao Zheng
Sa-Na Yang
Yan-Cheng Hu
Boshun Wan
Xiang-Ping Hu
Chunling Fu
Yankai Huang
Jian Zheng
Qing-An Chen
Shengming Ma
机构：
[1] Zhejiang University,Laboratory of Molecular Recognition and Synthesis, Department of Chemistry
[2] Chinese Academy of Sciences,Dalian Institute of Chemical Physics
[3] University of Chinese Academy of Sciences,undefined
来源：
Nature Chemistry | 2022年 / 14卷
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摘要：
Butafulvene is a constitutional isomer of benzene, comprising a cyclobutene skeleton bearing two exocyclic conjugated methylene units. As a result of the intrinsic high strain energy and anti-aromaticity, the preparation of butafulvene compounds has been a fundamental issue for the development of butafulvene chemistry. Here an efficient palladium-catalysed coupling protocol involving propargylic compounds has been developed, providing a solid and versatile strategy for the rapid assembly of symmetric butafulvene derivatives. Based on mechanistic studies, two complementary mechanisms, both involving palladium catalysis, have been confirmed. With the mechanism unveiled, the synthesis of non-symmetric butafulvenes has also been achieved. Advantages of this strategy include tolerance to a wide range of propargylic molecules, mild reaction conditions, simple catalytic systems and easy scalability. The synthetic potential of the products as platform molecules for cyclobutene derivatives has also been demonstrated.
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页码：1185 / 1192
页数：7
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共 149 条
[1]  
Wang M(2020)Methodologies and strategies for selective borylation of C–Het and C–C bonds Chem. Rev. 120 7348-7398
[2]  
Shi Z(2020)Transformations of less-activated phenols and phenol derivatives via C–O cleavage Chem. Rev. 120 10454-10515
[3]  
Qiu Z(2019)Beyond Friedel and Crafts: directed alkylation of C–H bonds in arenes Angew. Chem. Int. Ed. 58 7202-7236
[4]  
Li C-J(2018)Recent advances in chemical dearomatization of nonactivated arenes Chem. Soc. Rev. 47 7996-8017
[5]  
Evano G(2017)Oxidative C–H/C–H coupling reactions between two (hetero)arenes Chem. Rev. 117 8787-8863
[6]  
Theunissen C(2016)(Hetero)aromatics from dienynes, enediynes and enyne-allenes Chem. Soc. Rev. 45 4364-4390
[7]  
Wertjes WC(2015)Simple and efficient system for combined solar energy harvesting and reversible hydrogen storage J. Am. Chem. Soc. 137 7576-7579
[8]  
Southgate EH(2014)Chemicals from alkynes with palladium catalysts Chem. Rev. 114 1783-1826
[9]  
Sarlah D(2012)Asymmetric hydrogenation of heteroarenes and arenes Chem. Rev. 112 2557-2590
[10]  
Yang Y(2012)Beyond directing groups: transition-metal-catalyzed C–H activation of simple arenes Angew. Chem. Int. Ed. 51 10236-10254
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