One-Pot C-N/C-C Cross-Coupling of Methyliminodiacetic Acid Boronyl Arenes Enabled by Protective Enolization

被引：28
|
作者：
Grob, Jonathan E. [1 ]
Dechantsreiter, Michael A. [1 ]
Tichkule, Ritesh B. [1 ]
Connolly, Michael K. [1 ]
Honda, Ayako [1 ]
Tomlinson, Ronald C. [1 ]
Hamann, Lawrence G. [1 ]
机构：
[1] Novartis Inst BioMed Res Inc, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 21期
关键词：
MEDICINAL CHEMISTS; GENERAL STRATEGY; ARYL; TRIFLUOROMETHYLATION; ESTERS; COST;
D O I：
10.1021/ol302702q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Iterative cross-coupling is a highly efficient and versatile strategy for modular construction in organic synthesis, though this has historically been demonstrated solely in the context of C-C bond formation. A C-N cross-coupling of haloarene methyliminodiacetic acid (MIDA) boronates with a wide range of aromatic and aliphatic amines is reported. Successful cross-coupling of aliphatic amines was realized only through protective enolization of the MIDA group. This reaction paradigm was subsequently utilized to achieve a one-pot C-N/C-C cross-coupling sequence.
引用
收藏
页码：5578 / 5581
页数：4
相关论文
共 50 条
  • [41] One-Pot Access to peri-Condensed Heterocycles via Manganese-Catalyzed Cascade C-N and C-C Bond Formation
    Yu, Yunliang
    Feng, Yadong
    Chauvin, Remi
    Ma, Shuangshuang
    Wang, Lianhui
    Cui, Xiuling
    ORGANIC LETTERS, 2018, 20 (14) : 4209 - 4212
  • [42] A facile one pot C-C and C-N bond formation for the synthesis of spiro-benzodiazepines and their cytotoxicity
    Nagaraju, Burri
    Kovvuri, Jeshma
    Babu, K. Suresh
    Adiyala, Praveen Reddy
    Nayak, V. Lakshma
    Alarifi, Abdullah
    Kamal, Ahmed
    TETRAHEDRON, 2017, 73 (49) : 6969 - 6976
  • [43] A Strategy for the Formal C-N Cross-Coupling of Tertiary Amines
    Ledwith, Peter R.
    Cooney, Madelene L.
    Bahou, Karim A.
    Garcia-Carceles, Javier
    Thomson, Joshua
    Bower, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (50)
  • [44] Silicon-based C-N Cross-coupling Reaction
    Shimizu, Kenta
    Minami, Yasunori
    Goto, Osamu
    Ikehira, Hideyuki
    Hiyama, Tamejiro
    CHEMISTRY LETTERS, 2014, 43 (04) : 438 - 440
  • [45] Cross-coupling polycondensation via C-O or C-N bond cleavage
    Yang, Ze-Kun
    Xu, Ning-Xin
    Takita, Ryo
    Muranaka, Atsuya
    Wang, Chao
    Uchiyama, Masanobu
    NATURE COMMUNICATIONS, 2018, 9
  • [46] Copper Promoted C-N and C-O Type Cross-Coupling Reactions
    Das, Pralay
    Sharma, Dharminder
    Kumar, Manish
    Singh, Bikram
    CURRENT ORGANIC CHEMISTRY, 2010, 14 (08) : 754 - 783
  • [47] Copper-catalyzed general C-N and C-O bond cross-coupling with arylboronic acid
    Lam, PYS
    Vincent, G
    Clark, CG
    Deudon, S
    Jadhav, PK
    TETRAHEDRON LETTERS, 2001, 42 (20) : 3415 - 3418
  • [48] The Liebeskind-Srogl C-C Cross-Coupling Reaction
    Prokopcova, Hana
    Kappe, C. Oliver
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) : 2276 - 2286
  • [49] Transition-Metal-Free C-C, C-O, and C-N Cross-Couplings Enabled by Light
    Liu, Wenbo
    Li, Jianbin
    Querard, Pierre
    Li, Chao-Jun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (16) : 6755 - 6764
  • [50] Functionalized Pyrazoles as Agents in C-C Cross-Coupling Reactions
    Pejic, Marijana
    Popp, Sebastian
    Bolte, Michael
    Wagner, Matthias
    Lerner, Hans-Wolfram
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2014, 69 (01): : 83 - 97
12345