Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki-Miyaura Cross-Coupling Reactions

被引：31
|
作者：
Raushel, Jessica [1 ]
Sandrock, Deidre L. [1 ]
Josyula, Kanth V. [2 ]
Pakyz, Deborah [2 ]
Molander, Gary A. [1 ]
机构：
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
[2] Sigma Aldrich New Prod, Milwaukee, WI 53209 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 08期
基金：
美国国家科学基金会;
关键词：
AMINOMETHYLATIONS; SCOPE;
D O I：
10.1021/jo2001066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.
引用
收藏
页码：2762 / 2769
页数：8
相关论文
共 50 条
  • [31] 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
  • [32] 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
  • [33] 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
  • [34] 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
  • [35] 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
  • [36] 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
  • [37] Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides
    Molander, GA
    Felix, LA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10): : 3950 - 3956
  • [38] Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles
    Molander, Gary A.
    Brown, Adam R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26): : 9681 - 9686
  • [39] Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems
    Grasa, GA
    Viciu, MS
    Huang, JK
    Zhang, CM
    Trudell, ML
    Nolan, SP
    [J]. ORGANOMETALLICS, 2002, 21 (14) : 2866 - 2873
  • [40] Synthesis of enantiomerically enriched triarylmethanes by enantiospecific suzuki-miyaura cross-coupling reactions
    [J]. Crudden, C.M. (cruddenc@chem.queensu.ca), 1600, American Chemical Society (136):
12345