ortho-Acetoxylation of Phosphonic and Phosphoric Monoacids via Pd(II) Catalysis

被引：50
|
作者：
Chan, Li Yan [1 ]
Meng, Xiangjian [1 ]
Kim, Sunggak [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 17期
关键词：
WADSWORTH-EMMONS REACTION; ARYL HYDROGEN PHOSPHATES; H BOND ACTIVATION; DIRECTING GROUP; ORTHO-ARYLATION; C-O; OLEFINATION; COMPLEXES; MECHANISM; OXIDATION;
D O I：
10.1021/jo4011188
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient method is developed for Pd-catalyzed ortho-acetoxylation using organophosphates, namely, benzylic phosphonic and aryl phosphoric monoacids, as the directing group.
引用
收藏
页码：8826 / 8832
页数：7
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共 41 条
  • [1] THE ORTHO-ACETOXYLATION OF PHENOLS BY COPPER(II) ACETATE
    TAKIZAWA, Y
    TATEISHI, A
    SUGIYAMA, J
    YOSHIDA, H
    YOSHIHARA, N
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (02) : 104 - 105
  • [2] Catalytic Ortho-Acetoxylation of Masked Benzyl Alcohols via an Exo-Directing Mode
    Ren, Zhi
    Schulz, Jonathan E.
    Dong, Guangbin
    [J]. ORGANIC LETTERS, 2015, 17 (11) : 2696 - 2699
  • [3] Pd(II)-Catalyzed Acetoxylation of Uracil via Electrophilic Palladation
    Lee, Hyun Seung
    Kim, Se Hee
    Kim, Jae Nyoung
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (01): : 238 - 241
  • [4] Direct ortho-acetoxylation of anilides via palladium-catalyzed sp2 C-H bond oxidative activation
    Wang, Guan-Wu
    Yuan, Ting-Ting
    Wu, Xue-Liang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12): : 4717 - 4720
  • [5] Regioselective ortho-acetoxylation/methoxylation of N-(2-benzoylphenyl)benzamides via substrate directed C-H activation
    Reddy, B. V. Subba
    Revathi, G.
    Reddy, A. Srinivas
    Yadav, J. S.
    [J]. TETRAHEDRON LETTERS, 2011, 52 (45) : 5926 - 5929
  • [6] Palladium-Catalyzed Regioselective ortho-Acetoxylation of 3-Aryl-1,2,4-Benzotriazines via C-H Activation
    Ren, Xiaoyu
    Liu, Jin
    Yan, Hao
    Shi, Xiaokang
    Yang, Sizhuo
    Li, Jian
    Huang, Guosheng
    [J]. SYNLETT, 2013, 24 (11) : 1395 - 1398
  • [7] N-Directed Pd-Catalyzed Direct ortho-Acetoxylation and ortho-tert-Butoxylation of 2-Phenyl-4H-benzo[d][1,3]oxazin-4-ones via C-H Activation
    Gupta, Mohit
    Kumar, Sandeep
    Kumar, Prashant
    Singh, Amit Kumar
    Bahadur, Vijay
    Singh, Brajendra K.
    [J]. CHEMISTRYSELECT, 2019, 4 (47): : 13992 - 13997
  • [8] CATALYSIS BY PD(II)-CU(II) COMBINATION IN ACETIC MEDIA - ACETOXYLATION OF 2-METHYLENE-BICYCLO[2.2.1]HEPTANE SERIES OLEFINS
    CASTANET, Y
    PETIT, F
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1986, 35 (02): : 143 - 160
  • [9] Enantioselective desymmetrization of prochiral allenic diols via cooperative catalysis of Pd(OAc)2 and a chiral phosphoric acid
    Cao, Kou-Sen
    Zheng, Wen-Hua
    [J]. TETRAHEDRON-ASYMMETRY, 2015, 26 (20) : 1150 - 1155
  • [10] Ortho arylation of acetanilides via Pd(II)-catalyzed C-H functionalization
    Yang, Shangdong
    Li, Bijie
    Wan, Xiaobing
    Shi, Zhangjie
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (19) : 6066 - +
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