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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 06期

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

页码：2618 / 2623

页数：6

共 35 条

[1] Sulfonyl Fluoride Inhibitors of Fatty Acid Amide Hydrolase
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
[J]. 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
Borhade, Sanjay R.
Sandstrom, Anja
Arvidsson, Per I.
[J]. ORGANIC LETTERS, 2013, 15 (05) : 1056 - 1059
[3] BULLOUGH DA, 1986, J BIOL CHEM, V261, P5722
[4] Organic Synthesis "On Water"
Chanda, Arani
Fokin, Valery V.
[J]. CHEMICAL REVIEWS, 2009, 109 (02) : 725 - 748
[5] AFFINITY LABELING OF PURINE NUCLEOTIDE SITES IN PROTEINS
COLMAN, RF
[J]. ANNUAL REVIEW OF BIOCHEMISTRY, 1983, 52 : 67 - 91
[6] Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry
Dong, Jiajia
Krasnova, Larissa
Finn, M. G.
Sharpless, K. Barry
[J]. 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
Grimster, Neil P.
Connelly, Stephen
Baranczak, Aleksandra
Dong, Jiajia
Krasnova, Larissa B.
Sharpless, K. Barry
Powers, Evan T.
Wilson, Ian A.
Kelly, Jeffery W.
[J]. 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
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.
[J]. CHEMISTRY & BIOLOGY, 2013, 20 (04): : 541 - 548
[9] Selective Targeting of Distinct Active Site Nucleophiles by Irreversible Src-Family Kinase Inhibitors
Gushwa, Nathan N.
Kang, Sumin
Chen, Jing
Taunton, Jack
[J]. 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
Hanley, Patrick S.
Ober, Matthias S.
Krasovskiy, Arkady L.
Whiteker, Gregory T.
Kruper, William J.
[J]. ACS CATALYSIS, 2015, 5 (09): : 5041 - 5046

← 1 2 3 4 →