Palladium-Catalyzed Direct Arylation of C(sp3)-H Bonds of α-Cyano Aliphatic Amides

被引：56
|
作者：
Reddy, M. Damoder [1 ]
Watkins, E. Blake [1 ]
机构：
[1] Union Univ, Dept Pharmaceut Sci, Sch Pharm, Jackson, TN 38305 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 22期
关键词：
C-H BONDS; STEREOSELECTIVE-SYNTHESIS; AMINO-ACIDS; ALKYLATION; FUNCTIONALIZATION; ACTIVATION; CARBONYLATION; C(SP(2))-H; REDUCTION; 8-AMINOQUINOLINE;
D O I：
10.1021/acs.joc.5b02138
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pd(OAc)(2)-catalyzed arylation of C(sp(3))-H bonds in alpha-cyano-alpha-methyl aliphatic amides is achieved in the presence of 8-aminoquinoline, as a removable directing group, using Mn(OAc)(2) and Na2CO3. The current strategy enables the placement of an aryl/heteroaryl group at the beta-position of alpha-cyano aliphatic acids for the first time. Wide functional group tolerance and easily accessible starting materials provide an efficient protocol for the synthesis of arylated alpha-cyano amides. Furthermore, the synthetic utility of the products has been demonstrated by their efficient conversions to medicinally important alpha,alpha-dialkylated acid and beta-amino acid derivatives.
引用
收藏
页码：11447 / 11459
页数：13
相关论文
共 50 条
  • [1] Palladium-Catalyzed Asymmetric Arylation of C(sp3)-H Bonds of Aliphatic Amides: Controlling Enantioselectivity Using Chiral Phosphoric Amides/Acids
    Yan, Shao-Bai
    Zhang, Song
    Duan, Wei-Liang
    [J]. ORGANIC LETTERS, 2015, 17 (10) : 2458 - 2461
  • [2] A Simple Aliphatic Diamine Auxiliary for Palladium-Catalyzed Arylation of Unactivated β-C(sp3)-H Bonds
    Lou, Jiang
    Wang, Quannan
    He, Yuan
    Yu, Zhengkun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (23) : 4571 - 4584
  • [3] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12984 - 12986
  • [4] Palladium-Catalyzed Asymmetric C(sP3)-H Arylation
    Yamamoto, Takeshi
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (09) : 1045 - 1046
  • [5] Nickel-Catalyzed Direct C (sp3)-H Arylation of Aliphatic Amides with Thiophenes
    Wang, Xie
    Zhu, Longzhi
    Chen, Sihai
    Xu, Xinhua
    Au, Chak-Tong
    Qu, Renhua
    [J]. ORGANIC LETTERS, 2015, 17 (21) : 5228 - 5231
  • [6] Ligand-Enabled, Palladium-Catalyzed β-C(sp3)-H Arylation of Weinreb Amides
    Park, Hojoon
    Chekshin, Nikita
    Shen, Peng-Xiang
    Yu, Jin-Quan
    [J]. ACS CATALYSIS, 2018, 8 (10): : 9292 - 9297
  • [7] Asymmetric construction of quaternary α-nitro amides by palladium-catalyzed C(sp3)-H arylation
    Kong, Wei-Xin
    Xie, Shi-Jing
    Cao, Chen-Yao-Zi
    Zhang, Chao-Wei
    Wang, Chuanyong
    Duan, Wei-Liang
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (15) : 2292 - 2295
  • [8] Palladium-catalyzed intra- and intermolecular arylation of unactivated C(sp3)-H bonds
    Baudoin, Olivier
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [9] Nickel-Catalyzed Direct Thiolation of C(sp3)-H Bonds in Aliphatic Amides
    Wang, Xie
    Qiu, Renhua
    Yan, Chunyang
    Reddy, Vutukuri Prakash
    Zhu, Longzhi
    Xu, Xinhua
    Yin, Shuang-Feng
    [J]. ORGANIC LETTERS, 2015, 17 (08) : 1970 - 1973
  • [10] Nickel-Catalyzed Direct Thioetherification of β-C(Sp3)-H Bonds of Aliphatic Amides
    Lin, Cong
    Yu, Wenlong
    Yao, Jinzhong
    Wang, Bingjie
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. ORGANIC LETTERS, 2015, 17 (05) : 1340 - 1343
12345