Synthesis of aryl trimethylstannanes from aryl halides: an efficient photochemical method

被引：24
作者：
Chen, Kai [1 ]
He, Pei [1 ]
Zhang, Shuai [1 ]
Li, Pengfei [1 ]
机构：
[1] Xi An Jiao Tong Univ, FIST, Ctr Organ Chem, 99 Yanxiang Rd, Xian 710054, Shaanxi, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 58期
基金：
美国国家科学基金会;
关键词：
CROSS-COUPLING REACTIONS; C-H BORYLATION; CATALYZED STANNYLATION; STILLE REACTION; SOLAR-CELLS; ALKYNES; ARYLSTANNANES; FLUORINATION; STANNANES; GERMANIUM;
D O I：
10.1039/c6cc01135g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient transition-metal-free photochemical method featuring excellent functional group tolerance, mild reaction conditions and short reaction times has been discovered and developed for the synthesis of (hetero)aryl trimethylstannanes from (hetero)aryl halides. A photo-initiated radical chain mechanism was proposed based on preliminary mechanistic studies.
引用
收藏
页码：9125 / 9128
页数：4
相关论文
共 42 条
  • [1] Dithienogermole As a Fused Electron Donor in Bulk Heterojunction Solar Cells
    Amb, Chad M.
    Chen, Song
    Graham, Kenneth R.
    Subbiah, Jegadesan
    Small, Cephas E.
    So, Franky
    Reynolds, John R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) : 10062 - 10065
  • [2] Room-Temperature Photoinduced Direct C-H-Arylation via Base-Promoted Homolytic Aromatic Substitution
    Buden, Maria E.
    Guastavino, Javier F.
    Rossi, Roberto A.
    [J]. ORGANIC LETTERS, 2013, 15 (06) : 1174 - 1177
  • [3] Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
    Chen, Kai
    Zhang, Shuai
    He, Pei
    Li, Pengfei
    [J]. CHEMICAL SCIENCE, 2016, 7 (06) : 3676 - 3680
  • [4] Synthesis of arylstannanes from arylamines
    Chopa, AB
    Lockhart, MT
    Silbestri, G
    [J]. ORGANOMETALLICS, 2001, 20 (15) : 3358 - 3360
  • [5] A Synthetic Method for Palladium-Catalyzed Stannylation at the 5-and 6-Benzo Positions of Indoles
    Corcoran, Emily B.
    Williams, Anna B.
    Hanson, Robert N.
    [J]. ORGANIC LETTERS, 2012, 14 (17) : 4630 - 4633
  • [6] The Stille Reaction, 38 Years Later
    Cordovilla, Carlos
    Bartolome, Camino
    Martinez-Ilarduya, Jesus Ma
    Espinet, Pablo
    [J]. ACS CATALYSIS, 2015, 5 (05): : 3040 - 3053
  • [7] Copper-Catalyzed Boron-Selective C(sp2)-C(sp3) Oxidative Cross-Coupling of Arylboronic Acids and Alkyltrifluoroborates Involving a Single-Electron Transmetalation Process
    Ding, Siyi
    Xu, Liang
    Li, Pengfei
    [J]. ACS CATALYSIS, 2016, 6 (02): : 1329 - 1333
  • [8] Catalytic C-H Bond Stannylation: A New Regioselective Pathway to C-Sn Bonds via C-H Bond Functionalization
    Doster, Meghan E.
    Hatnean, Jillian A.
    Jeftic, Tamara
    Modi, Sunjay
    Johnson, Samuel A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) : 11923 - 11925
  • [9] The mechanisms of the Stille reaction
    Espinet, P
    Echavarren, AM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (36) : 4704 - 4734
  • [10] Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
12345