On-Water Synthesis of Biaryl Sulfonyl Fluorides

被引:46
作者
Chinthakindi, Praveen K. [1 ]
Kruger, Hendrik G. [1 ]
Govender, Thavendran [1 ]
Naicker, Tricia [1 ]
Arvidsson, Per I. [2 ,3 ]
机构
[1] Univ KwaZulu Natal, Catalysis & Peptide Res Unit, ZA-4041 Durban, South Africa
[2] Karolinska Inst, Drug Discovery & Dev Platform, Dept Med Biochem & Biophys, Sci Life Lab, SE-17121 Stockholm, Sweden
[3] Karolinska Inst, Div Translat Med & Chem Biol, Dept Med Biochem & Biophys, SE-17121 Stockholm, Sweden
基金
新加坡国家研究基金会;
关键词
CROSS-COUPLING REACTIONS; KINASE; ARYL; SULFONIMIDAMIDES; SITE; INACTIVATION; REACTIVITY; INHIBITORS; CHEMISTRY; SUBUNIT;
D O I
10.1021/acs.joc.5b02770
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report an efficient, ligand-free, and additive-free Suzuki-Miyaura coupling that is compatible with the aromatic sulfonyl fluoride functional group. The protocol proceeds at room temperature, on water, and offers facile access to a wide range of biaryl sulfonyl fluorides as bioorthogonal "click" reagents.
引用
收藏
页码:2618 / 2623
页数:6
相关论文
共 35 条
[1]   Sulfonyl Fluoride Inhibitors of Fatty Acid Amide Hydrolase [J].
Alapafuja, Shakiru O. ;
Nikas, Spyros P. ;
Bharathan, Indu T. ;
Shukla, Vidyanand G. ;
Nasr, Mahmoud L. ;
Bowman, Anna L. ;
Zvonok, Nikolai ;
Li, Jing ;
Shi, Xiaomeng ;
Engen, John R. ;
Makriyannis, Alexandros .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (22) :10074-10089
[2]   Synthesis of Novel Aryl and Heteroaryl Acyl Sulfonimidamides via Pd-Catalyzed Carbonylation Using a Nongaseous Precursor [J].
Borhade, Sanjay R. ;
Sandstrom, Anja ;
Arvidsson, Per I. .
ORGANIC LETTERS, 2013, 15 (05) :1056-1059
[3]  
BULLOUGH DA, 1986, J BIOL CHEM, V261, P5722
[4]   Organic Synthesis "On Water" [J].
Chanda, Arani ;
Fokin, Valery V. .
CHEMICAL REVIEWS, 2009, 109 (02) :725-748
[5]   AFFINITY LABELING OF PURINE NUCLEOTIDE SITES IN PROTEINS [J].
COLMAN, RF .
ANNUAL REVIEW OF BIOCHEMISTRY, 1983, 52 :67-91
[6]   Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry [J].
Dong, Jiajia ;
Krasnova, Larissa ;
Finn, M. G. ;
Sharpless, K. Barry .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9430-9448
[7]   Aromatic Sulfonyl Fluorides Covalently Kinetically Stabilize Transthyretin to Prevent Amyloidogenesis while Affording a Fluorescent Conjugate [J].
Grimster, Neil P. ;
Connelly, Stephen ;
Baranczak, Aleksandra ;
Dong, Jiajia ;
Krasnova, Larissa B. ;
Sharpless, K. Barry ;
Powers, Evan T. ;
Wilson, Ian A. ;
Kelly, Jeffery W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (15) :5656-5668
[8]   Chemical Proteomics with Sulfonyl Fluoride Probes Reveals Selective Labeling of Functional Tyrosines in Glutathione Transferases [J].
Gu, Christian ;
Shannon, D. Alexander ;
Colby, Tom ;
Wang, Zheming ;
Shabab, Mohammed ;
Kumari, Selva ;
Villamor, Joji Grace ;
McLaughlin, Christopher J. ;
Weerapana, Eranthie ;
Kaiser, Markus ;
Cravatt, Benjamin F. ;
van der Hoorn, Renier A. L. .
CHEMISTRY & BIOLOGY, 2013, 20 (04) :541-548
[9]   Selective Targeting of Distinct Active Site Nucleophiles by Irreversible Src-Family Kinase Inhibitors [J].
Gushwa, Nathan N. ;
Kang, Sumin ;
Chen, Jing ;
Taunton, Jack .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (50) :20214-20217
[10]   Nickel- and Palladium-Catalyzed Coupling of Aryl Fluorosulfonates with Aryl Boronic Acids Enabled by Sulfuryl Fluoride [J].
Hanley, Patrick S. ;
Ober, Matthias S. ;
Krasovskiy, Arkady L. ;
Whiteker, Gregory T. ;
Kruper, William J. .
ACS CATALYSIS, 2015, 5 (09) :5041-5046