Cross-dehydrogenative coupling of 3,6-dihydro-2H-pyrans with 1,3-dicarbonyls and aryl moieties

被引：4
作者：
Feng, Guidong [1 ]
Sun, Chuanxi [1 ]
Xin, Xiaodong [2 ]
Wan, Renzhong [1 ]
Liu, Lei [2 ]
机构：
[1] Shandong Agr Univ, Coll Anim Sci & Vet Med, Tai An 271018, Shandong, Peoples R China
[2] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Shandong, Peoples R China
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 23期
关键词：
Cross-dehydrogenative coupling; 3,6-Dihydro-2H-pyran; 1,3-Dicarbonyl; Aryl ring; C-H FUNCTIONALIZATION; TERTIARY-AMINES; STRUCTURALLY DIVERSE; BONDS ADJACENT; ASYMMETRIC-SYNTHESIS; BENZYL ETHERS; N-OXIDES; ALKYLATION; ARYLATION; CATALYSIS;
D O I：
10.1016/j.tetlet.2019.05.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An indium-catalyzed oxidative C-H alkylation and arylation of 4-substituted 3,6-dihydro-2H-pyrans (DHPs) using dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as the oxidant has been developed. The mild and modular cross-dehydrogenative coupling reaction exhibited a broad scope with respect to both DHPs and nucleophilic 1,3-dicarbonyl moieties as well as aryl rings, rapidly providing 2,4-disubstituted DHPs bearing diverse patterns of functionalities at the alpha position. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1547 / 1550
页数：4
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共 81 条
  • [1] Regioselectivity in the formation of small- and medium-sized cyclic ethers by diene-ene ring-closing metathesis
    Basu, S
    Waldmann, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10) : 3977 - 3979
  • [2] A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline
    Boess, Esther
    Schmitz, Corinna
    Klussmann, Martin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) : 5317 - 5325
  • [3] Structurally Diverse α-Substituted Benzopyran Synthesis through a Practical Metal-Free C(sp3)-H Functionalization
    Chen, Wenfang
    Xie, Zhiyu
    Zheng, Hongbo
    Lou, Hongxiang
    Liu, Lei
    [J]. ORGANIC LETTERS, 2014, 16 (22) : 5988 - 5991
  • [4] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
    Cho, Seung Hwan
    Kim, Ji Young
    Kwak, Jaesung
    Chang, Sukbok
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
  • [5] Iron-catalyzed direct α-arylation of ethers with azoles
    Correa, Arkaitz
    Fiser, Bela
    Gomez-Bengoa, Enrique
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (69) : 13365 - 13368
  • [6] Visible light-promoted C-H functionalization of ethers and electron-deficient arenes
    Devari, Shekaraiah
    Shah, Bhahwal Ali
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (07) : 1490 - 1493
  • [7] Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis
    DiRocco, Daniel A.
    Rovis, Tomislav
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) : 8094 - 8097
  • [8] Strategy and methodology development for the total synthesis of polyether ionophore antibiotics
    Faul, MM
    Huff, BE
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 2407 - 2473
  • [9] Cationic Iron(III) Porphyrin-Catalyzed [4+2] Cycloaddition of Unactivated Aldehydes with Simple Dienes
    Fujiwara, Kyohei
    Kurahashi, Takuya
    Matsubara, Seijiro
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) : 5512 - 5515
  • [10] Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms
    Ghobrial, Michael
    Schnuerch, Michael
    Mihovilovic, Marko D.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) : 8781 - 8793
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