Palladium-Catalyzed Enantioselective Directed C(sp3)-H Functionalization Using C5-Substituted 8-Aminoquinoline Auxiliaries

被引：4
作者：
Huang, Yi [1 ,2 ]
Lv, Xiaoyan [1 ,2 ]
Tong, Hua-Rong [1 ,2 ]
He, Wenji [1 ,2 ]
Bai, Ziqian [1 ,2 ]
Wang, Hao [1 ,2 ]
He, Gang [1 ,2 ]
Chen, Gong [1 ,2 ,3 ,4 ]
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Frontiers Sci Ctr New Organ Matter, Tianjin 300071, Peoples R China
[4] Haihe Lab Sustainable Chem Transformat, Tianjin 300192, Peoples R China
来源：
ORGANIC LETTERS | 2023年 / 26卷 / 01期
基金：
中国国家自然科学基金; 国家重点研发计划;
关键词：
C-H BONDS; UNACTIVATED C(SP(3))-H; ASYMMETRIC FUNCTIONALIZATION; C(SP(2))-H BONDS; ARYLATION; ALKOXYLATION; BIDENTATE;
D O I：
10.1021/acs.orglett.3c03688
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
8-Aminoquinoline (AQ) has proven to be a highly effective bidentate directing group for palladium-catalyzed C-H functionalization reactions. However, enantiocontrol of AQ-directed C(sp(3))-H functionalization reactions has been challenging. Herein, a new protocol is presented for the Pd-catalyzed enantioselective arylation of unactivated beta C(sp(3))-H bonds of alkyl carboxamides with aryl iodides using a C-5-iodinated 8-aminoquinolines (IQ) auxiliary in conjugation with a BINOL ligand. Additionally, a C-5-aryl substituted 8-aminoquinoline auxiliary can facilitate enantioselective alkenylation and alkynylation of benzylic C(sp(3))-H bonds of 3-arylpropanamides with the corresponding bromide reagents under similar conditions.
引用
收藏
页码：94 / 99
页数：6
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  • [1] Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis
    Bai, Zibo
    Zhang, Heng
    Wang, Hao
    Yu, Hanrui
    Chen, Gong
    He, Gang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (02) : 1195 - 1202
  • [2] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers
    Chen, Fa-Jie
    Zhao, Sheng
    Hu, Fang
    Chen, Kai
    Zhang, Qi
    Zhang, Shuo-Qing
    Shi, Bing-Feng
    [J]. CHEMICAL SCIENCE, 2013, 4 (11) : 4187 - 4192
  • [3] Palladium-Catalyzed Methionine-Facilitated β and γ C(sp3)-H Arylation of N-Terminal Aliphatic Amino Acids of Peptides
    Chen, Xiangxiang
    Li, Bo
    Tong, Huarong
    Qi, Liping
    He, Gang
    Chen, Gong
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (21) : 2502 - 2506
  • [4] Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds
    Daugulis, Olafs
    Roane, James
    Tran, Ly Dieu
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) : 1053 - 1064
  • [5] Pd(II)-Catalyzed Tandem Enantioselective Methylene C(sp3)-H Alkenylation-Aza-Wacker Cyclization to Access β-Stereogenic γ-Lactams
    Ding, Yi
    Han, Ye-Qiang
    Wu, Le-Song
    Zhou, Tao
    Yao, Qi-Jun
    Feng, Ya-Lan
    Li, Ya
    Kong, Ke-Xin
    Shi, Bing-Feng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (33) : 14060 - 14064
  • [6] Facile Benzo-Ring Construction via Palladium-Catalyzed Functionalization of Unactivated sp3 C-H Bonds under Mild Reaction Conditions
    Feng, Yiqing
    Wang, Yuji
    Landgraf, Bradley
    Liu, Shi
    Chen, Gong
    [J]. ORGANIC LETTERS, 2010, 12 (15) : 3414 - 3417
  • [7] Total Synthesis and Structural Revision of the Piperarborenines via Sequential Cyclobutane C-H Arylation
    Gutekunst, Will R.
    Baran, Phil S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (47) : 19076 - 19079
  • [8] Pd(II)-Catalyzed Enantioselective Alkynylation of Unbiased Methylene C(sp3)-H Bonds Using 3,3′-Fluorinated-BINOL as a Chiral Ligand
    Han, Ye-Qiang
    Ding, Yi
    Zhou, Tao
    Yan, Sheng-Yi
    Song, Hong
    Shi, Bing-Feng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (11) : 4558 - 4563
  • [9] Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp3 C-H Functionalization
    He, Gang
    Wang, Bo
    Nack, William A.
    Chen, Gong
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (04) : 635 - 645
  • [10] A Practical Strategy for the Structural Diversification of Aliphatic Scaffolds through the Palladium-Catalyzed Picolinamide-Directed Remote Functionalization of Unactivated C(sp3)-H Bonds
    He, Gang
    Chen, Gong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5192 - 5196
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