Deoxygenative cross-coupling of aryl ketones with (Hetero)arenes mediated by a TiCl4/Ammonia borane system

被引：0
|
作者：
Zang, Yong-jun [1 ]
Zhou, Shi-jie [1 ]
Qian, Chen [1 ]
Xu, Qi-lin [1 ]
Li, Guo-si [1 ]
Li, Xing [2 ]
Zhu, Fu-cheng [1 ]
机构：
[1] West Anhui Univ, Dept Biol & Pharmaceut Engn, Anhui Prov Key Lab Qual Evaluat & Improvement Trad, Luan 237012, Anhui, Peoples R China
[2] Taizhou Univ, Lege Pharm & Chem & Chem Engn, Taizhou 225300, Jiangsu, Peoples R China
来源：
TETRAHEDRON | 2024年 / 163卷
基金：
中国国家自然科学基金;
关键词：
Deoxygenative coupling; Aromatic ketones; Ammonia borane; Titanium tetrachloride; FRIEDEL-CRAFTS ALKYLATION; REDUCTIVE ALKYLATION; ARENES; TRIARYLMETHANES; INDOLES;
D O I：
10.1016/j.tet.2024.134147
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and mild protocol for the direct deoxygenative coupling of aryl ketones with electron-rich (hetero) arenes to construct the C(sp2)- 2 )- C(sp3) 3 ) bond was achieved, which was mediated by TiCl4 4 and by using ammonia borane (AB) as the reductant. This strategy provides a novel protocol for the synthesis of unsymmetrical diaryland triarylmethanes.
引用
收藏
页数：6
相关论文
共 42 条
  • [31] Preparation of a Stable Trifluoroborate Salt for the Synthesis of 1-Aryl-2,2-difluoro-enolethers and/or 2,2-Difluoro-1-aryl-ketones via Palladium-Mediated Cross-Coupling
    Katz, Jason D.
    Lapointe, Blair T.
    Dinsmore, Christopher J.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22): : 8866 - 8869
  • [32] Highly Diastereoselective Cobalt-Mediated C(sp3)-C(sp2) Cross-Coupling Reactions of Cyclic Halohydrins with (Hetero) Aryl Grignard Reagents
    Hammann, Jeffrey M.
    Haas, Diana
    Steib, Andreas K.
    Knochel, Paul
    SYNTHESIS-STUTTGART, 2015, 47 (10): : 1461 - 1468
  • [33] Palladium-Catalyzed Cross-Coupling of 4-(Tosyloxy)quinazolines with H-Phosphonates and Phosphine Oxides: An Efficient Access to 2-(Hetero)aryl-4-phosphorylated Quinazolines
    Ye, Xinglin
    Huang, Jian
    Deng, Zhihong
    Peng, Yiyuan
    SYNTHESIS-STUTTGART, 2022, 54 (03): : 788 - 796
  • [34] Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions
    Kravchenko, Marionella A.
    Verbitskiy, Egor V.
    Medvinskiy, Igor D.
    Rusinov, Gennady L.
    Charushin, Valery N.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (14) : 3118 - 3120
  • [35] Construction of Di(hetero)arylmethanes Through Pd-Catalyzed Direct Dehydroxylative Cross-Coupling of Benzylic Alcohols and Aryl Boronic Acids Mediated by Sulfuryl Fluoride (SO2F2)
    Zhao, Chuang
    Zha, Gao-Feng
    Fang, Wan-Yin
    Rakesh, K. P.
    Qin, Hua-Li
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (08) : 1801 - 1807
  • [36] A highly efficient and recyclable Pd(PPh3)4/PEG-400 system for Stille cross-coupling reactions of organostannanes with aryl bromides
    Huang, Xue
    Yao, Fang
    Wei, Ting
    Cai, Mingzhong
    JOURNAL OF CHEMICAL RESEARCH, 2017, (09) : 547 - 550
  • [37] A convenient synthesis of 4(5)-(hetero)aryl-1H-imidazoles via microwave-assisted Suzuki-Miyaura cross-coupling reaction (vol 55, pg 6347, 2014)
    Vichier-Guerre, Sophie
    Dugue, Laurence
    Pochet, Sylvie
    TETRAHEDRON LETTERS, 2014, 55 (51) : 7140 - 7140
  • [38] Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: efficient synthetic methods for diaryl ketones and chalcones at room temperature
    Ogawa, Daisuke
    Hyodo, Keita
    Suetsugu, Masato
    Li, Jing
    Inoue, Yoshiaki
    Fujisawa, Mamoru
    Iwasaki, Masayuki
    Takagi, Kentaro
    Nishihara, Yasushi
    TETRAHEDRON, 2013, 69 (12) : 2565 - 2571
  • [39] DNA-encoded focused indazole library synthesis by a palladium- mediated C-N(sp2) cross-coupling reaction between DNA-linked (hetero)aryl halides and aromatic nitrogen heterocycles
    Yang, Juan
    Xia, Shengdi
    Liu, Jiaxiang
    Yu, Zikun
    Mei, Lianghe
    Lu, Weiwei
    Chen, Yulin
    Chen, Shaopeng
    Wang, Xuan
    Lu, Xiaojie
    TETRAHEDRON LETTERS, 2022, 96
  • [40] Copper-Catalyzed Oxidative Cross-Coupling/C-C Bond Cleavage/Cyclization of Aryl Methyl Ketones with 4-Aminocoumarins: Domino Synthesis of Dicoumarin-Fused [1,5]-Diazocines
    Peng, Fei
    Li, Lili
    Liu, Jin
    Chen, Zhiwei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (08) : 1667 - 1673
12345