Rhodium-Catalyzed Tandem Cyclization/Si-C Activation Reaction for the Synthesis of Siloles

被引:57
作者
Zhang, Qing-Wei [1 ,2 ]
An, Kun [1 ,2 ]
He, Wei [1 ,2 ]
机构
[1] Tsinghua Univ, Sch Med, Beijing 100084, Peoples R China
[2] Tsinghua Univ, Tsinghua Peking Joint Ctr Life Sci, Beijing 100084, Peoples R China
基金
中国博士后科学基金;
关键词
heterocycles; luminescence; rhodium; silicon; synthetic methods; CARBON-SILICON BOND; BENZOSILOLE DERIVATIVES; PHOTOPHYSICAL PROPERTIES; ASYMMETRIC-SYNTHESIS; ALKYNES; CLEAVAGE; CYCLOADDITION; POLYMERS; SILANES; SILAFLUORENES;
D O I
10.1002/anie.201400828
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Siloles represent an important emerging class of photoluminescent materials. Reported herein is a new synthetic strategy involving a tandem cyclization/Si-C activation reaction featuring high efficiency, wide substrate scope, and practical utility. This method enabled the first synthesis of benzofuran siloles as well as rapid access to conjugated siloles. During the course of the study we also uncovered an unusual yet general Si-C(sp(2)) activation in the presence of p acids.
引用
收藏
页码:5667 / 5671
页数:5
相关论文
共 64 条
  • [1] [Anonymous], 2010, ANGEW CHEM, V122, P10361
  • [2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
    Barder, TE
    Walker, SD
    Martinelli, JR
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
  • [3] Silole-containing polymers: Chemistry and optoelectronic properties
    Chen, Junwu
    Cao, Yong
    [J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (17) : 1714 - 1742
  • [4] How dual bridging atoms tune structural and optoelectronic properties of ladder-type heterotetracenes?-a theoretical study
    Chen, Xian-Kai
    Zou, Lu-Yi
    Ren, Ai-Min
    Fan, Jian-Xun
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (43) : 19490 - 19498
  • [5] Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3%
    Chu, Ta-Ya
    Lu, Jianping
    Beaupre, Serge
    Zhang, Yanguang
    Pouliot, Jean-Remi
    Wakim, Salem
    Zhou, Jiayun
    Leclerc, Mario
    Li, Zhao
    Ding, Jianfu
    Tao, Ye
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) : 4250 - 4253
  • [6] Coffin RC, 2009, NAT CHEM, V1, P657, DOI [10.1038/NCHEM.403, 10.1038/nchem.403]
  • [7] Siloles: Part 1: Synthesis, Characterization, and Applications
    Corey, Joyce Y.
    [J]. ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 59, 2011, 59 : 1 - 180
  • [8] STABLE HOMOLEPTIC METAL ALKYLS
    DAVIDSON, PJ
    LAPPERT, MF
    PEARCE, R
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (07) : 209 - 217
  • [9] Stereochemical control in organic synthesis using silicon-containing compounds
    Fleming, I
    Barbero, A
    Walter, D
    [J]. CHEMICAL REVIEWS, 1997, 97 (06) : 2063 - 2192
  • [10] Synthesis and characterization of perfluoroaryl-substituted siloles and thiophenes: A series of electron-deficient blue light emitting materials
    Geramita, Katharine
    McBee, Jennifer
    Shen, Yulong
    Radu, Nora
    Tilley, T. Don
    [J]. CHEMISTRY OF MATERIALS, 2006, 18 (14) : 3261 - 3269