Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments

被引:125
|
作者
Blangetti, Marco [1 ]
Rosso, Helena [2 ]
Prandi, Cristina [2 ]
Deagostino, Annamaria [2 ]
Venturello, Paolo [2 ]
机构
[1] Natl Univ Ireland Univ Coll Dublin, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland
[2] Univ Turin, Dept Chem, I-10125 Turin, Italy
关键词
Suzuki-Miyaura cross-coupling; acylation; palladium; ketones; PALLADIUM-CATALYZED CARBONYLATION; PREPARING AROMATIC KETONES; ASYMMETRIC CONJUGATE ADDITION; FRIEDEL-CRAFTS ACYLATION; ARYLBORONIC ACIDS; ACYL CHLORIDES; BORONIC ACIDS; NAZAROV REACTION; CARBOXYLIC ANHYDRIDES; ORGANOBORON COMPOUNDS;
D O I
10.3390/molecules18011188
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.
引用
收藏
页码:1188 / 1213
页数:26
相关论文
共 50 条
  • [31] ORGN 675-Scope of the Suzuki-Miyaura cross-coupling reaction of potassium trifluoroboratohomoenolates
    Molander, Gary A.
    Jean-Gerard, Ludivine
    Petrillo, Daniel E.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [32] Strategies towards Chemoselective Suzuki-Miyaura Cross-Coupling
    Fyfe, James W. B.
    Watson, Allan J. B.
    [J]. SYNLETT, 2015, 26 (09) : 1139 - 1144
  • [33] Functionalization and Suzuki-Miyaura cross-coupling of potassium organotrifluoroborates
    Canturk, Belgin
    Molander, Gary A.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238 : 56 - 56
  • [34] Homogeneous and Recyclable Palladium Catalysts: Application in Suzuki-Miyaura Cross-Coupling Reactions
    King, Andrew K.
    Brar, Aneelman
    Li, Guigen
    Findlater, Michael
    [J]. ORGANOMETALLICS, 2023, 42 (17) : 2353 - 2358
  • [35] ORGN 734-New substrates for Suzuki-Miyaura cross-coupling reactions
    Boudreault, Pierre-Luc
    Voyer, Normand
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [36] Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions
    Frese, Marcel
    Schnepel, Christian
    Minges, Hannah
    Voss, Hauke
    Feiner, Rebecca
    Sewald, Norbert
    [J]. CHEMCATCHEM, 2016, 8 (10) : 1799 - 1803
  • [37] Modular Dihydrobenzoazaphosphole Ligands for Suzuki-Miyaura Cross-Coupling
    Zhang, Yongda
    Lao, Kendricks S.
    Sieber, Joshua D.
    Xu, Yibo
    Wu, Linglin
    Wang, Xiao-Jun
    Desrosiers, Jean-Nicolas
    Lee, Heewon
    Haddad, Nizar
    Han, Zhengxu S.
    Yee, Nathan K.
    Song, Jinhua J.
    Howell, Amy R.
    Senanayake, Chris H.
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (22): : 4429 - 4434
  • [38] Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling
    Kemker, Isabell
    Schnepel, Christian
    Schroeder, David C.
    Marion, Antoine
    Sewald, Norbert
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (16) : 7417 - 7430
  • [39] Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides
    Zhou, Tongliang
    Xie, Pei-Pei
    Ji, Chong-Lei
    Hong, Xin
    Szostak, Michal
    [J]. ORGANIC LETTERS, 2020, 22 (16) : 6434 - 6440
  • [40] Melamine as a versatile ligand for Suzuki-Miyaura cross-coupling
    Trafford, Mitchell A.
    Hamilton, Alaina E.
    Buxton, Audrey M.
    Chalker, Justin M.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245