Methodology to Control the Regioselective Installation of a Carboxylic Acid for the Synthesis of 2,3-Diarylpropionic Acids

被引：0
|
作者：
Hamilton, Mason D. [1 ]
Perrone, Trina M. [1 ]
Popp, Brian V. [1 ]
机构：
[1] West Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26505 USA
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2025年 / 367卷 / 04期
基金：
美国国家科学基金会;
关键词：
C-C bond formation; Organoboron; Carboxylation; Palladium catalysis; Regioselectivity; ALKENES; HYDROCARBOXYLATION; RECEPTOR;
D O I：
10.1002/adsc.202400952
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A stepwise copper-catalyzed boracarboxylation then palladium-catalyzed Suzuki-Miyaura cross-coupling methodology was developed to access 2,3-diarylpropionic acid derivatives regioselectively by pre-setting the position of the carboxylic acid in the boracarboxylation reaction. This method provides access to a wide range of aryl and heteroaryl products in up to 80% isolated yield. Pharmaceutical potential was demonstrated by synthesizing a glucagon receptor antagonist drug in three steps (31% overall yield) from commercially available 4-tert-butylstyrene.
引用
收藏
页数：6
相关论文
共 50 条
  • [21] Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid
    Malhotra, Rajesh
    Dey, Tushar K.
    Dutta, Swarup
    Basu, Sourav
    Hajra, Saumen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (33) : 6507 - 6515
  • [22] Diastereoselective Protocols for the Synthesis of 2,3-trans- and 2,3-cis-6-Methoxy-morpholine-2-carboxylic Acid Derivatives
    Penso, Michele
    Foschi, Francesca
    Pellegrino, Sara
    Testa, Andrea
    Gelmi, Maria Luisa
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07): : 3454 - 3461
  • [23] REGIOSELECTIVE SYNTHESIS OF PYRIDO[2,3-D]PYRIMIDINES
    ANDERSON, GL
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (05) : 1469 - 1470
  • [24] Regioselective synthesis of quinolone antibacterials via borate complex of quinolone carboxylic acid
    Heravi, MM
    Jaddi, ZS
    Oskooie, HA
    Khaleghi, S
    Ghassemzadeh, M
    JOURNAL OF CHEMICAL RESEARCH-S, 2005, (09): : 578 - 579
  • [25] Regioselective synthesis of ortho-iodobiphenylboronic acid derivatives: a superior catalyst for carboxylic acid activation
    Al-Zoubi, Raed M.
    Al-Jammal, Walid K.
    McDonald, Robert
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (09) : 3612 - 3623
  • [26] A NOVEL METHODOLOGY FOR THE SYNTHESIS OF BETA-AMINO ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE FUNCTIONALIZATION OF LINEAR DICARBOXYLIC-ACID DERIVATIVES
    SIBI, MP
    DESHPANDE, PK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 156 - ORGN
  • [27] Synthesis of thieno[2,3-b]pyrrole-2(4)-carboxylic and 2,4-dicarboxylic acids
    Grozav, Alina N.
    Fedoriv, Mariana Z.
    Chornous, Vitaliy A.
    Palamar, Alina A.
    Bratenko, Mykhailo K.
    Vovk, Mykhailo V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (4-5) : 435 - 441
  • [28] Synthesis of thieno[2,3-b]pyrrole-2(4)-carboxylic and 2,4-dicarboxylic acids
    Alina N. Grozav
    Mariana Z. Fedoriv
    Vitaliy A. Chornous
    Alina A. Palamar
    Mykhailo K. Bratenko
    Mykhailo V. Vovk
    Chemistry of Heterocyclic Compounds, 2019, 55 : 435 - 441
  • [29] Novel regioselective hydroxylations of pyridine carboxylic acids at position C2 and pyrazine carboxylic acids at position C3
    Tinschert, A
    Tschech, A
    Heinzmann, K
    Kiener, A
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2000, 53 (02) : 185 - 195
  • [30] Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO2
    Greenhalgh, Mark D.
    Thomas, Stephen P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) : 11900 - 11903
12345