Photoinduced Transition-Metal-Free Cross-Coupling of Aryl Halides with H-Phosphonates

被引:92
|
作者
Zeng, Huiying [1 ]
Dou, Qian [1 ]
Li, Chao-Jun [1 ,2 ,3 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, 222 Tianshui Rd, Lanzhou 730000, Gansu, Peoples R China
[2] McGill Univ, Dept Chem, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada
[3] McGill Univ, FQRNT Ctr Green Chem & Catalysis, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada
关键词
CATALYST-FREE; ROOM-TEMPERATURE; DIRECT ARYLATION; P-ARYLATION; BUTOXIDE; TRIFLUOROMETHYLATION; DIPHENYLPHOSPHINE; BONDS; OXIDE;
D O I
10.1021/acs.orglett.8b04081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photoinduced transition-metal- and photosensitizer-free cross coupling of aryl halides (including Ar-Cl, Ar-Br, and Ar-I) with H-phosphonates (including dialkyl phosphonates and diarylphosphine oxides) is reported. Various functional groups were tolerated, including ester, methoxy, dimethoxy, alkyl, phenyl, trifluoromethyl, and heterocyclic compounds. This simple and green strategy provides a practical pathway to synthesize arylphosphine oxides.
引用
收藏
页码:1301 / 1305
页数:5
相关论文
共 50 条
  • [41] Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds
    Stephens, Thomas C.
    Pattison, Graham
    ORGANIC LETTERS, 2017, 19 (13) : 3498 - 3501
  • [42] Photoinduced Cross-Coupling of Aryl Iodides with Alkenes
    Liu, Yuliang
    Li, Haoyu
    Chiba, Shunsuke
    ORGANIC LETTERS, 2021, 23 (02) : 427 - 432
  • [43] Transition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond
    Guolin Li
    Yexenia Nieves-Quinones
    Hui Zhang
    Qingjin Liang
    Shuaisong Su
    Qingchao Liu
    Marisa C. Kozlowski
    Tiezheng Jia
    Nature Communications, 11
  • [44] A Transition-Metal-Free Cross-Coupling Reaction of Allylic Bromides with Aryl- and Vinylboronic Acids (vol 23, pg 1085, 2012)
    Ueda, Mitsuhiro
    Nishimura, Kota
    Kashima, Ryo
    Ryu, Ilhyong
    SYNLETT, 2012, (20) : 3001 - 3001
  • [45] Transition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond
    Li, Guolin
    Nieves-Quinones, Yexenia
    Zhang, Hui
    Liang, Qingjin
    Su, Shuaisong
    Liu, Qingchao
    Kozlowski, Marisa C.
    Jia, Tiezheng
    NATURE COMMUNICATIONS, 2020, 11 (01)
  • [46] Aryl H-phosphonates .7. Studies on the formation of phosphorus-carbon bond in the reaction of trityl and benzyl halides with dialkyl and diphenyl H-phosphonates
    Kers, A
    Stawinski, J
    Dembkowski, L
    Kraszewski, A
    TETRAHEDRON, 1997, 53 (37) : 12691 - 12698
  • [47] Photoinduced transition metal-free borylation of aryl halides in an aqueous phase
    Liu, Mengqi
    Cheng, Wan-Min
    Li, Zi-Long
    Jiang, Hong
    Ma, Jimei
    GREEN CHEMISTRY, 2025, 27 (14) : 3634 - 3639
  • [48] Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides
    Ma Wei-Yuan
    Dai Huifang
    Kang Shaolin
    Zhang Tianlin
    Shu Xing-Zhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (10) : 3614 - 3622
  • [49] A dehydrogenative cross-coupling reaction between aromatic aldehydes or ketones and dialkyl H-phosphonates for formyl or acylphenylphosphonates
    Huang, Xing-Fen
    Wu, Qing-Lai
    He, Jian-Shi
    Huang, Zhi-Zhen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (15) : 4466 - 4472
  • [50] Dehydrative Cross-Coupling for C-N Bond Construction under Transition-Metal-Free Conditions
    Xing, Huicong
    Chen, Meijuan
    Zhang, Dong
    Geng, Zhishuai
    Xie, Peizhong
    Loh, Teck-Peng
    ORGANIC LETTERS, 2022, 24 (31) : 5657 - 5662