Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units.
The main purpose of this video is to show 6 reaction steps of a convergent synthesis and prepare a complex molecule containing up to three nonplanar polyaromatic units, which are two corannulene moieties and a racemic hexahelicene linking them. The compound described in this work is a good host for fullerenes. Several common organic reactions, such as free-radical reactions, C-C coupling or click chemistry, are employed demonstrating the versatility of functionalization that this compound can accept. All of these reactions work for planar aromatic molecules. With subtle modifications, it is possible to achieve similar results for nonplanar polyaromatic compounds.
GIR MIOMeT, IU CINQUIMA, Área de Química Inorgánica, Universidad de Valladolid; celedonio.alvarez@uva.es.
Celedonio M
CM
Álvarez
GIR MIOMeT, IU CINQUIMA, Área de Química Inorgánica, Universidad de Valladolid.
Héctor
H
Barbero
GIR MIOMeT, IU CINQUIMA, Área de Química Inorgánica, Universidad de Valladolid.
Sergio
S
Ferrero
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D011084:Polycyclic Aromatic Hydrocarbons; D011083:Polycyclic Compounds; C434863:corannulene; C031660:helicenes; D003300:Copper
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26352025
Chem Soc Rev. 2013 Apr 7;42(7):2592-609
23229523
Chem Soc Rev. 2011 Oct;40(10):5084-121
21655588
Chem Rev. 2006 Dec;106(12):4868-84
17165678
Adv Mater. 2010 Sep 8;22(34):3839-56
20717982
Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7786-90
23765590
J Am Chem Soc. 2015 Jul 8;137(26):8469-74
25928194
Org Lett. 2015 Jun 5;17(11):2578-81
25985189
J Am Chem Soc. 2007 Apr 4;129(13):3842-3
17348661
Chem Commun (Camb). 2010 Jul 21;46(27):4853-65
20498918
J Org Chem. 2005 Aug 5;70(16):6158-63
16050672
Angew Chem Int Ed Engl. 2010;49(1):31-3
19921729
J Phys Chem B. 2014 Oct 16;118(41):11956-64
25248285
Angew Chem Int Ed Engl. 2003 Sep 5;42(34):3986-9
12973757
J Am Chem Soc. 2005 May 25;127(20):7272-3
15898750
Angew Chem Int Ed Engl. 2001 Jun 1;40(11):2004-2021
11433435
J Am Chem Soc. 2005 Mar 30;127(12):4345-9
15783216
Org Lett. 2003 Jul 24;5(15):2595-7
12868867
Angew Chem Int Ed Engl. 2000 Jun 2;39(11):1921-1923
10940981
Org Lett. 2015 Nov 6;17(21):5292-5
26485442
J Chem Phys. 2004 Jan 22;120(4):2042-8
15268340
Chem Soc Rev. 2007 Feb;36(2):189-97
17264922
Chem Rev. 2006 Dec;106(12):4843-67
17165677
Nanoscale. 2013 Mar 7;5(5):1727-52
23381727
J Am Chem Soc. 2006 May 31;128(21):6870-84
16719467
Chem Soc Rev. 2008 Aug;37(8):1512-9
18648677
J Am Chem Soc. 2014 Apr 16;136(15):5555-8
24670158
Top Curr Chem. 2014;349:63-120
24797233
Chem Rev. 2012 Mar 14;112(3):1463-535
22017405
Chem Rev. 2006 Dec;106(12):5250-73
17165687
Dalton Trans. 2014 Nov 14;43(42):15693-6
25181755
Adv Mater. 2007 Oct 19;19(20):3214-3228
18846263
J Am Chem Soc. 2001 Dec 26;123(51):12770-4
11749533
J Am Chem Soc. 2014 Sep 17;136(37):13045-52
25154039
Org Biomol Chem. 2015 Sep 14;13(34):9035-41
26220565