Lewis acid InBr3-catalyzed arylation of diorgano diselenides and ditellurides with arylboronic acids

被引:49
作者
Ren, Kai [1 ]
Wang, Min [1 ]
Wang, Lei [1 ,2 ]
机构
[1] Huaibei Coal Teachers Coll, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED SYNTHESIS; CROSS-COUPLING REACTIONS; DIPHENYL DISELENIDE; ARYL IODIDE; DIARYL SELENIDES; SE-SE; ENANTIOSELECTIVE ALLYLATION; NUCLEOPHILIC-SUBSTITUTION; STEREOSELECTIVE-SYNTHESIS; CONVENIENT SYNTHESIS;
D O I
10.1039/b914533h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel Lewis acid InBr3-catalyzed direct cross-coupling reaction of arylboronic acids with diorgano diselenides and ditellurides without any additive has been developed. The reactions generated the corresponding unsymmetrical diorgano monoselenides and monotellurides in good to excellent yields. The method has advantages of broad substrate scope, simple operation, mild reaction conditions and high effectiveness. A possible reaction mechanism was proposed.
引用
收藏
页码:4858 / 4861
页数:4
相关论文
共 84 条
  • [1] A Facile One-Pot Preparation of Organoselanyltrifluoroborates from Dihalobenzenes and Their Cross-Coupling Reaction
    Ahn, Hong Ryul
    Cho, Young Ae
    Kim, Dong-Su
    Chin, Jungwook
    Gyoung, Young-Soo
    Lee, Seokjoon
    Kang, Heonjoong
    Ham, Jungyeob
    [J]. ORGANIC LETTERS, 2009, 11 (02) : 361 - 364
  • [2] Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent
    Ajiki, K
    Hirano, M
    Tanaka, K
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4193 - 4195
  • [3] Synthesis and free radical polymerization of p-methylseleno- and p-phenylselenostyrenes
    Ando, T
    Kwon, TS
    Kitagawa, A
    Tanemura, T
    Kondo, S
    Kunisada, H
    Yuki, Y
    [J]. MACROMOLECULAR CHEMISTRY AND PHYSICS, 1996, 197 (09) : 2803 - 2810
  • [4] [Anonymous], 1999, ORGANOSELENIUM CHEM
  • [5] Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions
    Babu, G
    Perumal, PT
    [J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3225 - 3228
  • [6] A novel synthesis of allyl and propargyl selenides in aqueous media promoted by indium
    Bao, WL
    Zheng, YF
    Zhang, YM
    Zhou, JQ
    [J]. TETRAHEDRON LETTERS, 1996, 37 (52) : 9333 - 9334
  • [7] CARBON-HETEROATOM BOND-FORMING REDUCTIVE ELIMINATION - MECHANISM, IMPORTANCE OF TRAPPING REAGENTS, AND UNUSUAL ELECTRONIC EFFECTS DURING FORMATION OF ARYL SULFIDES
    BARANANO, D
    HARTWIG, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) : 2937 - 2938
  • [8] Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides
    Barder, TE
    Buchwald, SL
    [J]. ORGANIC LETTERS, 2004, 6 (16) : 2649 - 2652
  • [9] Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones
    Batey, RA
    Thadani, AN
    Smil, DV
    [J]. ORGANIC LETTERS, 1999, 1 (10) : 1683 - 1686
  • [10] Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes
    Bieber, LW
    da Silva, MF
    Menezes, PH
    [J]. TETRAHEDRON LETTERS, 2004, 45 (13) : 2735 - 2737