Calcium-Mediated C-H and C-F Bond Cleavage: Synthesis of Indenes and Perfluorodibenzopentalenes from 1,4-Dilithio-1,3-butadienes

被引:14
作者
Wei, Baosheng [1 ]
Li, Heng [1 ]
Zhang, Wen-Xiong [1 ]
Xi, Zhenfeng [1 ,2 ]
机构
[1] Peking Univ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, BNLMS,Minist Educ, Beijing 100871, Peoples R China
[2] Chinese Acad Sci, SIOC, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
ALKALI-METAL COMPOUNDS; DI-LITHIO REAGENTS; STRUCTURAL-CHARACTERIZATION; FACILE SYNTHESIS; ORGANOMETALLIC COMPOUNDS; COMPLEXES; CATALYSTS; ROUTE; METALLOCENES; REACTIVITY;
D O I
10.1021/acs.organomet.6b00073
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The development of Ca-mediated reactions is of great importance and is in great demand in both organometallic and organic chemistry. In this paper, we report that calcium iodide efficiently promotes the transformation of various 1,4-dilithio-1,3-butadienes into indenes or perfluorodibenzopentalenes, via an intramolecular C-H or C-F bond cleavage, respectively. In the reaction process, the Ca-induced s-cis/trans configurational isomerization of 1,4-dilithio-1,3-butadienes is followed by the subsequent nucleophilic C-H or C-F bond activation.
引用
收藏
页码:1458 / 1463
页数:6
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[1]   Effect of the nature of metallocene complexes of group IV metals on their performance in catalytic ethylene and propylene polymerization [J].
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SANTI, S ;
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Gambaro, A ;
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Gobetto, R ;
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Venzo, A .
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[10]   The B(C6F5)3 Boron Lewis Acid Route to Arene-Annulated Pentalenes [J].
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