TMSCl-Promoted Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine

被引:19
|
作者
Tanaka, Hideo [1 ]
Yano, Tomotake [1 ]
Kobayashi, Kazuma [1 ]
Kamenoue, Syogo [1 ]
Kuroboshi, Manabu [1 ]
Kawakubo, Hiromu [2 ]
机构
[1] Okayama Univ, Grad Sch Nat Sci & Technol, Okayama 7008530, Japan
[2] Asahi Kasei Chem Corp, API Dept, Chiyoda Ku, Tokyo 1018101, Japan
关键词
reduction; electron transfer; phosphorus; silicon; TERTIARY PHOSPHINE OXIDES; REDUCTION; EFFICIENT; VERBINDUNGEN; RESOLUTION; SECONDARY; REAGENT;
D O I
10.1055/s-0030-1259529
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct reductive transformation of triphenylphosphine oxide to triphenylphosphine was performed successfully by electrolysis with TMSCl in an acetonitrile/Bu4NBr/(Zn anode)-(Pt cathode)/undivided cell/constant current electrolysis system. A plausible ECEC mechanism involving the formation of silylated phosphorus radical is proposed.
引用
收藏
页码:582 / 584
页数:3
相关论文
共 50 条
  • [1] Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine in the Presence of Chlorotrimethylsilane
    Kawakubo, Hiromu
    Kuroboshi, Manabu
    Yano, Tomotake
    Kobayashi, Kazuma
    Kamenoue, Syogo
    Akagi, Tomomi
    Tanaka, Hideo
    [J]. SYNTHESIS-STUTTGART, 2011, (24): : 4091 - 4098
  • [2] Direct and Scalable Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine
    Manabe, Shuhei
    Wong, Curt M.
    Sevov, Christo S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (06) : 3024 - 3031
  • [3] ELECTROCHEMISTRY OF ORGANOPHOSPHORUS COMPOUNDS .2. ELECTROREDUCTION OF TRIPHENYLPHOSPHINE AND TRIPHENYLPHOSPHINE OXIDE
    SANTHANAM, KS
    BARD, AJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (05) : 1118 - +
  • [4] Electroreduction of triphenylphosphine dichloride and the efficient one-pot reductive conversion of phosphine oxide to triphenylphosphine
    Yano, Tomotake
    Kuroboshi, Manabu
    Tanaka, Hideo
    [J]. TETRAHEDRON LETTERS, 2010, 51 (04) : 698 - 701
  • [5] DERIVATIVES OF TRIPHENYLPHOSPHINE AND TRIPHENYLPHOSPHINE OXIDE
    SENEAR, AE
    VALIENT, W
    WIRTH, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (11): : 2001 - 2006
  • [6] Electroreduction of tetra-coordinate phosphonium derivatives; one-pot transformation of triphenylphosphine oxide into triphenylphosphine
    Kuroboshi, Manabu
    Yano, Tomotake
    Kamenoue, Shogo
    Kawakubo, Hiromu
    Tanaka, Hideo
    [J]. TETRAHEDRON, 2011, 67 (32) : 5825 - 5831
  • [7] SYNTHESIS OF TRIPHENYLPHOSPHINE FROM TRIPHENYLPHOSPHINE OXIDE
    WUNSCH, G
    WINTERSB.K
    GEIERHAA.H
    [J]. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1969, 369 (1-2): : 33 - &
  • [8] TMSCl-promoted selective oxidation of sulfides to sulfoxides with hydrogen peroxide
    Bahrami, Kiumars
    Khodaei, Mohammad M.
    Yousefi, Behrooz H.
    Arabi, Mehdi Sheikh
    [J]. TETRAHEDRON LETTERS, 2010, 51 (52) : 6939 - 6941
  • [9] ENTHALPIES OF COMBUSTION OF TRIPHENYLPHOSPHINE AND TRIPHENYLPHOSPHINE OXIDE
    KIRKLIN, DR
    DOMALSKI, ES
    [J]. JOURNAL OF CHEMICAL THERMODYNAMICS, 1988, 20 (06): : 743 - 754
  • [10] Beyond Triphenylphosphine: Advances on the Utilization of Triphenylphosphine Oxide
    Zhang, Jian-Qiu
    Han, Li-Biao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (04): : 2090 - 2103