Synthetic Utilization of Polynitroaromatic Compounds. 6. Remarkable Regioselectivity in Nucleophilic Displacement of Aromatic Nitro Groups with Amines

2008 ◽  
Vol 73 (6) ◽  
pp. 2285-2291 ◽  
Author(s):  
Konstantine A. Kislyi ◽  
Alexander V. Samet ◽  
Yuri A. Strelenko ◽  
Victor V. Semenov
Keyword(s):  
Nucleophilic Displacement ◽  
Aromatic Nitro ◽  
Synthetic Utilization

Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups

2005 ◽  
Vol 70 (23) ◽  
pp. 9371-9376 ◽  
Author(s):  
Alexander V. Samet ◽  
Victor N. Marshalkin ◽  
Konstantine A. Kislyi ◽  
Natalya B. Chernysheva ◽  
Yuri A. Strelenko ◽  
...  
Keyword(s):  
Nucleophilic Displacement ◽  
Synthetic Utilization

Nucleophilic displacement of aromatic nitro groups

Tetrahedron ◽  
1978 ◽  
Vol 34 (14) ◽  
pp. 2057-2068 ◽  
Author(s):  
James R. Beck
Keyword(s):  
Nucleophilic Displacement ◽  
Aromatic Nitro

ChemInform Abstract: REGIOSPECIFICITY IN NUCLEOPHILIC DISPLACEMENT OF AROMATIC NITRO GROUPS

1983 ◽  
Vol 14 (2) ◽  
Author(s):  
F. BENEDETTI ◽  
D. R. MARSHALL ◽  
C. J. M. STIRLING ◽  
J. L. LENG
Keyword(s):  
Nucleophilic Displacement ◽  
Aromatic Nitro

Synthetic Utilization of Polynitroaromatic Compounds. Part 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups.

ChemInform ◽  
2006 ◽  
Vol 37 (12) ◽  
Author(s):  
Alexander V. Samet ◽  
Victor N. Marshalkin ◽  
Konstantine A. Kislyi ◽  
Natalya B. Chernysheva ◽  
Yuri A. Strelenko ◽  
...  
Keyword(s):  
Nucleophilic Displacement ◽  
Synthetic Utilization

Bifluoride Ion Mediated SuFEx Trifluoromethylation of Sulfonyl Fluorides and Iminosulfur Oxydifluorides

2018 ◽  
Author(s):  
Christopher J. Smedley ◽  
Bing Gao ◽  
Suhua Li ◽  
Qinheng Zheng ◽  
Andrew Molino ◽  
...  
Keyword(s):  
Breast Cancer Cells ◽  
Catalytic Mechanism ◽  
Bioactive Molecules ◽  
Chromatographic Purification ◽  
Rapid Exchange ◽  
Nucleophilic Displacement ◽  
Sulfur Fluoride ◽  
Reactions With Nucleophiles ◽  
New Generation ◽  
Selection Of

Sulfur-Fluoride Exchange (SuFEx) is the new generation click chemistry transformation exploiting the unique properties of S-F bonds and their ability to undergo near-perfect reactions with nucleophiles. We report here the first SuFEx based protocol for the efficient synthesis of pharmaceutically important triflones and bis(trifluoromethyl)sulfur oxyimines from the corresponding sulfonyl fluorides and iminosulfur oxydifluorides, respectively. The new protocol involves the rapid exchange of the S-F bond with trifluoromethyltrimethylsilane (TMSCF<sub>3</sub>) upon activation with potassium bifluoride in anhydrous DMSO. The reaction tolerates a wide selection of substrates and proceeds under mild conditions without need for chromatographic purification. A tentative catalytic mechanism is proposed supported by DFT calculations, involving formation of the free trifluoromethyl anion followed by nucleophilic displacement of the S-F through a five-coordinate intermediate. The preparation of a benzothiazole derived bis(trifluoromethyl)sulfur oxyimine with cytotoxic selectivity for MCF7 breast cancer cells demonstrates the utility of this methodology for the late-stage functionalization of bioactive molecules.<br>

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