Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne

doi:10.1007/s40242-016-6071-0

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (3): 366-372.doi: 10.1007/s40242-016-6071-0

Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne

LI Junqiu¹, ZHANG Jiqian², QU Hongmei¹, LIU Jun¹, LI Juan¹, ZHOU Lishan³

1. Key Laboratory of Systems Bioengineering, Ministry of Education, Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
2. Nantong Dongchang Chemical Industrial Co., Ltd., Nantong 226407, P. R. China;
3. CNOOC Tianjin Chemical Research and Design Institute, Tianjin 300131, P. R. China

收稿日期:2016-03-01 修回日期:2016-03-28 出版日期:2016-06-01 发布日期:2016-04-05
通讯作者: QU Hongmei E-mail:ququhongmei@126.com
基金资助:
Supported by the National Natural Science Foundation of China(No.21102099).

Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne

LI Junqiu¹, ZHANG Jiqian², QU Hongmei¹, LIU Jun¹, LI Juan¹, ZHOU Lishan³

1. Key Laboratory of Systems Bioengineering, Ministry of Education, Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
2. Nantong Dongchang Chemical Industrial Co., Ltd., Nantong 226407, P. R. China;
3. CNOOC Tianjin Chemical Research and Design Institute, Tianjin 300131, P. R. China

Received:2016-03-01 Revised:2016-03-28 Online:2016-06-01 Published:2016-04-05
Contact: QU Hongmei E-mail:ququhongmei@126.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21102099).

摘要/Abstract

摘要：

Based on the formation of 2,5-bis(trimethylsilyl)-zirconacyclopentadienes from two silylalkynes with Cp₂ZrBu₂ and the Cu-mediated formation of 1,4-disilylbenzene via the cycloaddition of zirconacyclopentadienes to disubstituted alkynes, a selective synthesis of 1,4-dialkyl(aryl)-hexa-substituted benzenes was achieved followed by iodination and coupling reaction. The coupling reactions were carried out with either organolithium reagent or organozinc reagent(Negishi coupling), depending on the electrophilic species.

关键词: Zirconium, Hexa-substituted benzene, Iodination, Coupling reaction

Abstract:

Key words: Zirconium, Hexa-substituted benzene, Iodination, Coupling reaction

LI Junqiu, ZHANG Jiqian, QU Hongmei, LIU Jun, LI Juan, ZHOU Lishan. Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne[J]. 高等学校化学研究, 2016, 32(3): 366-372.

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Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne

Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne

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