Metal-free one-pot α-benzoxylation of benzylic alcohols with acids or aldehydes

被引:7
|
作者
Zhu, Yefu
Zheng, Yong
Song, Weibin
Wei, Bole
Xuan, Lijiang [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China
关键词
nBu(4)NI; TBHP; alpha-Benzoxy ketones; Cross-dehydrogenative coupling; DEHYDROGENATIVE COUPLING CDC; TERT-BUTYL HYDROPEROXIDE; C-H BONDS; CARBOXYLIC-ACIDS; CARBONYL-COMPOUNDS; TRANSITION-METAL; EFFICIENT SYNTHESIS; ACETOXY KETONES; OXIDATION; ACYLATION;
D O I
10.1016/j.tetlet.2017.12.030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free strategy has been developed for alpha-benzoxylation of benzylic alcohols with acids or aldehydes. The reaction proceeds via sequential oxidation and alpha-benzoxylation in one pot. Importantly, the reactions are performed in metal-free condition and utilize cheap aqueous TBHP as an oxidant, affording alpha-benzoxy ketones in moderate to good yields. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:368 / 371
页数:4
相关论文
共 50 条
  • [31] One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
    Leas, Derek A.
    Dong, Yuxiang
    Vennerstrom, Jonathan L.
    Stack, Douglas E.
    ORGANIC LETTERS, 2017, 19 (10) : 2518 - 2521
  • [32] Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols
    Casnati, Alessandra
    Lichosyt, Dawid
    Lainer, Bruno
    Veth, Lukas
    Dydio, Pawel
    ORGANIC LETTERS, 2021, 23 (09) : 3502 - 3506
  • [33] NBS/DBU mediated one-pot synthesis of α-acyloxyketones from benzylic secondary alcohols and carboxylic acids
    Zhu, Minghui
    Wei, Wei
    Yang, Daoshan
    Cui, Hong
    Cui, Huanhuan
    Sun, Xuejun
    Wang, Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (46) : 10998 - 11001
  • [35] A novel one-pot conversion of aldehydes to trifluoromethylated bromoallylic alcohols
    Shen, YC
    Zhang, YM
    ORGANIC LETTERS, 2001, 3 (18) : 2805 - 2806
  • [36] One-pot synthesis of epoxides from benzyl alcohols and aldehydes
    Alfonzo, Edwin
    Mendoza, Jesse W. L.
    Beeler, Aaron B.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 2308 - 2312
  • [37] Metal-Free One-Pot Domino Synthesis of Oxazolidinethione Derivatives of Quaternary Amino Acids from α-Amino Esters and Aldehydes Using CS2
    Shinde, Dinesh R.
    Krishna, Gamidi Rama
    Marelli, Udaya Kiran
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 7109 - 7114
  • [38] Oxidative decarboxylation of arylacetic acids in water: One-pot transition-metal-free synthesis of aldehydes and ketones
    Mete, Trimbak B.
    Khopade, Tushar M.
    Bhat, Ramakrishna G.
    TETRAHEDRON LETTERS, 2017, 58 (29) : 2822 - 2825
  • [39] Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes
    Teodoro, Bruno V. M.
    Silva, Luiz F., Jr.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22): : 11787 - 11791
  • [40] Metal-free aerobic one-pot synthesis of substituted/annulated quinolines from alcohols via indirect Friedlander annulation
    Anand, Namrata
    Koley, Suvajit
    Ramulu, B. Janaki
    Singh, Maya Shankar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (37) : 9570 - 9574