3-Amino-1-methyl-1H-pyridin-2-one-Directed PcII Catalysis: C(sp3)-H Activated Diverse Arylation Reaction

被引：33
作者：
Pati, Tanmay K. [1 ,2 ]
Debnath, Sudipto [1 ]
Kundu, Mrinalkanti [2 ]
Khamrai, Uttam [2 ]
Maiti, Dilip K. [1 ]
机构：
[1] Univ Calcutta, Dept Chem, 92 APC Rd, Kolkata 700009, India
[2] TCG Lifesci Private Ltd, Sect 5, Kolkata 700091, India
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 13期
关键词：
C-H BONDS; GAMMA-ARYLATION; FUNCTIONALIZATION; OLEFINATION; SP(2); ARYL; ACETOXYLATION; ALKENYLATION; PYRROLIDONES; ALKYLATION;
D O I：
10.1021/acs.orglett.8b01618
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new bidentate directing group, 3-amino-1-methyl-1Hpyridin-2-one, is introduced to achieve a powerful Pd-II metallacycle for selective gamma-C(sp(3)) H activation and arylation of aromatic and aliphatic carboxylic acid derivatives. The versatility of the directing group is validated for remote arylation of beta-C(sp(3))-H, beta-C(sp(2))-H, and gamma-C(sp(2))-H to achieve therapeutically important 2-pyridone analogues and arylated acid synthons. The traceless removal of the directing group to retrieve the directing element and carboxylic acids makes this method more interesting.
引用
收藏
页码：4062 / 4066
页数：5
相关论文
共 49 条
  • [1] RIGID 5-MEMBERED AND 6-MEMBERED C,N,N'-BOUND ARYL, BENZYL, AND ALKYL ORGANOPALLADIUM COMPLEXES - SP(2) VS SP(3) C-H ACTIVATION DURING CYCLOPALLADATION AND PALLADIUM(IV) INTERMEDIATES IN OXIDATIVE ADDITION-REACTIONS WITH DIHALOGENS AND ALKYL-HALIDES
    ALSTERS, PL
    ENGEL, PF
    HOGERHEIDE, MP
    COPIJN, M
    SPEK, AL
    VANKOTEN, G
    [J]. ORGANOMETALLICS, 1993, 12 (05) : 1831 - 1844
  • [2] [Anonymous], NATURE, DOI [10.1038/446001a, DOI 10.1038/446001A]
  • [3] NONPEPTIDIC INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE .3. DESIGN, SYNTHESIS, X-RAY CRYSTALLOGRAPHIC ANALYSIS, AND STRUCTURE-ACTIVITY-RELATIONSHIPS FOR A SERIES OF ORALLY-ACTIVE 3-AMINO-6-PHENYLPYRIDIN-2-ONE TRIFLUOROMETHYL KETONES
    BERNSTEIN, PR
    ANDISIK, D
    BRADLEY, PK
    BRYANT, CB
    CECCARELLI, C
    DAMEWOOD, JR
    EARLEY, R
    EDWARDS, PD
    FEENEY, S
    GOMES, BC
    KOSMIDER, BJ
    STEELMAN, GB
    THOMAS, RM
    VACEK, EP
    VEALE, CA
    WILLIAMS, JC
    WOLANIN, DJ
    WOOLSON, SA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (20) : 3313 - 3326
  • [4] Ligand-Enabled β-C-H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary
    Chen, Gang
    Shigenari, Toshihiko
    Jain, Pankaj
    Zhang, Zhipeng
    Jin, Zhong
    He, Jian
    Li, Suhua
    Mapelli, Claudio
    Miller, Michael M.
    Poss, Michael A.
    Scola, Paul M.
    Yeung, Kap-Sun
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) : 3338 - 3351
  • [5] Crabtree R. H., 2010, CHEM REV, V110, P575
  • [6] 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
  • [7] Chelation-Assisted Palladium-Catalyzed γ-Arylation of Aliphatic Carboxylic Acid Derivatives
    Dey, Aniruddha
    Pimparkar, Sandeep
    Deb, Arghya
    Guin, Srimanta
    Maiti, Debabrata
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (08) : 1301 - 1307
  • [8] A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds
    Do, Hien-Ouang
    Khan, Rana M. Kashif
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 15185 - 15192
  • [9] Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions
    Engle, Keary M.
    Mei, Tian-Sheng
    Wasa, Masayuki
    Yu, Jin-Quan
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 788 - 802
  • [10] Palladium-Catalyzed Direct Functionalization of 2-Aminobutanoic Acid Derivatives: Application of a Convenient and Versatile Auxiliary
    Fan, Mengyang
    Ma, Dawei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (46) : 12152 - 12155
12345