One-Step Synthesis of Benzophosphole Derivatives from Arylalkynes by Phosphenium-Dication-Mediated Sequential C-P/C-C Bond Forming Reaction

被引:12
|
作者
Nishimura, Kazutoshi [1 ]
Xu, Shibo [2 ]
Nishii, Yuji [1 ]
Hirano, Koji [1 ,2 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTRI, Innovat Catalysis Sci Div, Suita, Osaka 5650871, Japan
关键词
FRIEDEL-CRAFTS REACTION; FACILE SYNTHESIS; OXIDES; CYCLIZATION; RING;
D O I
10.1021/acs.orglett.3c00263
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free, phosphenium-dication-mediated sequential C-P and C-C bond forming reaction has been developed. This protocol can provide concise access to the (di)benzophosphole derivatives in one synthetic operation from the readily available and simple arylalkynes and phosphinic acids. Application to the multiple cyclization reaction and the fully intermolecular three-component coupling-type reaction are also described.
引用
收藏
页码:1503 / 1508
页数:6
相关论文
共 50 条
  • [31] SEQUENTIAL ALKOXY RADICAL FRAGMENTATION - A ONE-STEP METHOD FOR BREAKING 2 1,3-POSITIONED C-C BONDS
    BOTO, A
    BETANCOR, C
    HERNANDEZ, R
    RODRIGUEZ, MS
    SUAREZ, E
    TETRAHEDRON LETTERS, 1993, 34 (30) : 4865 - 4868
  • [32] Expeditious Synthesis of Isoquinolone Derivatives by Rhodium(I)-Catalyzed Annulation Reaction through C-C Bond Cleavage
    He, Yiyi
    Yuan, Chengsha
    Jiang, Zeqi
    Shuai, Li
    Xiao, Qing
    ORGANIC LETTERS, 2019, 21 (01) : 185 - 189
  • [33] Visible-Light-Induced Cascade Reaction of Isocyanides and N-Arylacrylamides with Diphenylphosphine Oxide via Radical C-P and C-C Bond Formation
    Li, Chun-Xiao
    Tu, De-Shuang
    Yao, Rui
    Yan, Hong
    Lu, Chang-Sheng
    ORGANIC LETTERS, 2016, 18 (19) : 4928 - 4931
  • [34] Phosphinoferrocenyl-terminated amidoamines:: Synthesis and catalytic utilization in palladium-mediated C-C bond forming reactions
    Kuehnert, Janett
    Lamac, Martin
    Demel, Jan
    Nicolai, Anja
    Lang, Heinrich
    Stepnicka, Petr
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 285 (1-2) : 41 - 47
  • [35] Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C-C Bond Forming Reactions
    Savela, Risto
    Mendez-Galvez, Carolina
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (17) : 5344 - 5378
  • [36] Transition-metal/Lewis acid free synthesis of acyl benzothiophenes via C-C bond forming reaction
    Pal, Sarbani
    Khan, Mohammad Ashrafuddin
    Bindu, P.
    Dubey, P. K.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2007, 3
  • [37] Copper(I)-mediated C-N/C-C Bond-forming Reaction with Tetrafluoroethylene for the Synthesis of N-Fluoroalkyl Heteroarenes via an Azacupration/Coupling Mechanism
    Ishida, Naoyoshi
    Adachi, Takuya
    Iwamoto, Hiroaki
    Ohashi, Masato
    Ogoshi, Sensuke
    CHEMISTRY LETTERS, 2021, 50 (03) : 442 - 444
  • [38] Stabilized Naked Sub-nanometric Cu Clusters within a Polymeric Film Catalyze C-N, C-C, C-O, C-S, and C-P Bond-Forming Reactions
    Oliver-Messeguer, Judit
    Liu, Lichen
    Garcia-Garcia, Saray
    Canos-Gimenez, Claudia
    Dominguez, Irene
    Gavara, Rafael
    Domenech-Carbo, Antonio
    Concepcion, Patricia
    Leyva-Perez, Antonio
    Corma, Avelino
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (11) : 3894 - 3900
  • [39] Metal-Free, Visible-Light-Promoted Synthesis of 3-Phosphorylated Coumarins via Radical C-P/C-C Bond Formation
    Liu, Dan
    Chen, Jian-Qiang
    Wang, Xing-Zhi
    Xu, Peng-Fei
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (16) : 2773 - 2777
  • [40] Coupling of cyclobutenediones with Fischer carbene complexes: A one-step synthesis of cyclopentenediones and/or 5-alkylidenefuranones via net insertion of the carbene unit into a C-C bond
    Zora, M
    Li, YH
    Herndon, JW
    ORGANOMETALLICS, 1999, 18 (21) : 4429 - 4436