Sumanene Hexaester: An Electron-Deficient Buckybowl

Hideaki Toda; Yuta Uetake; Yumi Yakiyama; Hironobu Nakazawa; Takashi Kajitani; Takanori Fukushima; Hidehiro Sakurai

doi:10.1055/s-0039-1690206

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(24): 4576-4581
DOI: 10.1055/s-0039-1690206

paper

Sumanene Hexaester: An Electron-Deficient Buckybowl

Hideaki Toda

^aDivision of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan eMail: hsakurai@chem.eng.osaka-u.ac.jp

,

Yuta Uetake

^aDivision of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan eMail: hsakurai@chem.eng.osaka-u.ac.jp

,

Yumi Yakiyama

^aDivision of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan eMail: hsakurai@chem.eng.osaka-u.ac.jp

,

Hironobu Nakazawa

^aDivision of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan eMail: hsakurai@chem.eng.osaka-u.ac.jp

,

Takashi Kajitani

^bLaboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan

,

Takanori Fukushima

^bLaboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan

,

Hidehiro Sakurai∗

^aDivision of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan eMail: hsakurai@chem.eng.osaka-u.ac.jp

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

2,3,5,6,8,9-Hexakis(phenoxycarbonyl)sumanene, a hexasubstituted sumanene with CO₂Ph groups at the peripheral aromatic carbons, was successfully prepared in good yield by Pd-catalyzed phenoxycarbonylation using a solvent of phenyl formate. Single-crystal X-ray structural analysis of this compound revealed the formation of a one-dimensional columnar structure, stacked in a staggered manner. The UV and emission spectra of this showed clear red-shifts compared with those of pristine sumanene, indicating the extension of the conjugation system.

Key words

sumanene - buckybowls - palladium catalysis - phenoxycarbonylation - electron-deficient polycyclic aromatic hydrocarbons - columnar packing structure

Volltext

Referenzen

References

Selected reviews on PAHs:

1a Scott LT, Bronstein HE, Preda DV, Ansems RB. M, Bratcher MS, Hagen S. Pure Appl. Chem. 1999; 71: 209
1b Watson MD, Fechtenkötter A, Müllen K. Chem. Rev. 2001; 101: 1267
1c Tsefrikas VM, Scott LT. Chem. Rev. 2006; 106: 4868
1d Wu J, Pisula W, Müllen K. Chem. Rev. 2007; 107: 718
1e Sygula A. Eur. J. Org. Chem. 2011; 1611
1f Chen L, Hernandez Y, Feng X, Müllen K. Angew. Chem. Int. Ed. 2012; 51: 7640
1g Sun Z, Ye Q, Chi C, Wu J. Chem. Soc. Rev. 2012; 41: 7857
1h Wang C, Dong H, Hu W, Liu Y, Zhu D. Chem. Rev. 2012; 112: 2208
1i Segawa Y, Ito H, Itami K. Nat. Rev. Mater. 2016; 1: 15002

2a Rohr U, Schlichting P, Böhm A, Gross M, Meerholz K, Bräuchle C, Müllen K. Angew. Chem. Int. Ed. 1998; 37: 1434
2b Langhals H, Kirner S. Eur. J. Org. Chem. 2000; 365
2c Hirayama S, Sakai H, Araki Y, Tanaka M, Imakawa M, Wada T, Takenobu T, Hasobe T. Chem. Eur. J. 2014; 20: 9081
2d Vollbrecht J, Bock H, Wiebeler C, Schumacher S, Kitzerow H. Chem. Eur. J. 2014; 20: 12026
2e Vollbrecht J, Wiebeler C, Neuba A, Bock H, Schumacher S, Kitzerow H. J. Phys. Chem. C 2016; 120: 7839
2f Vollbrecht J, Blazy S, Dierks P, Peurifoy S, Bock H, Kitzerow H. ChemPhysChem 2017; 18: 2024

3a Hassheider T, Benning SA, Kitzerow H.-S, Achard M.-F, Bock H. Angew. Chem. Int. Ed. 2001; 40: 2060
3b Bock H, Rajaoarivelo M, Clavaguera S, Grelet É. Eur. J. Org. Chem. 2006; 2889
3c Grelet É, Bock H. Europhys. Lett. 2006; 73: 712
3d Saïdi-Besbes S, Grelet É, Bock H. Angew. Chem. Int. Ed. 2006; 45: 1783
3e Alibert-Fouet A, Seguy I, Bobo J.-F, Destruel P, Bock H. Chem. Eur. J. 2007; 13: 1746
3f Grelet E, Dardel S, Bock H, Goldmann M, Lacaze E, Nallet F. Eur. Phys. J. E 2010; 31: 343
3g Osawa T, Kajitani T, Hashizume D, Ohsumi H, Sasaki S, Takata M, Koizumi Y, Saeki A, Seki S, Fukushima T, Aida T. Angew. Chem. Int. Ed. 2012; 51: 7990
3h Ferreira M, Moreira TS, Cristiano R, Gallardo H, Bentaleb A, Dechambenoit P, Hillard EA, Durola F, Bock H. Chem. Eur. J. 2018; 24: 2214

Selected reviews on buckybowls:

4a Scott LT. Pure Appl. Chem. 1996; 68: 291
4b Wu Y.-T, Siegel JS. Chem. Rev. 2006; 106: 4843
4c Amaya T, Hirao T. Chem. Commun. 2011; 47: 10524
4d Higashibayashi S, Sakurai H. Chem. Lett. 2011; 40: 122
4e Schmidt BM, Lentz D. Chem. Lett. 2014; 43: 171
4f Saito M, Shinokubo H, Sakurai H. Mater. Chem. Front. 2018; 2: 635

5a Imamura K, Takimiya K, Aso Y, Otsubo T. Chem. Commun. 1999; 1859
5b Furukawa S, Kobayashi J, Kawashima T. J. Am. Chem. Soc. 2009; 131: 14192
5c Saito M, Tanikawa T, Tajima T, Guo JD, Nagase S. Tetrahedron Lett. 2010; 51: 672
5d Furukawa S, Kobayashi J, Kawashima T. Dalton Trans. 2010; 39: 9329
5e Tanikawa T, Saito M, Guo JD, Nagase S. Org. Biomol. Chem. 2011; 9: 1731
5f Tan Q, Higashibayashi S, Karanjit S, Sakurai H. Nat. Commun. 2012; 3: 891
5g Tanikawa T, Saito M, Guo JD, Nagase S, Minoura M. Eur. J. Org. Chem. 2012; 7135
5h Li X, Zhu Y, Shao J, Wang B, Zhang S, Shao Y, Jin X, Yao X, Fang R, Shao X. Angew. Chem. Int. Ed. 2014; 53: 535
5i Ito S, Tokimatsu Y, Nozaki K. Angew. Chem. Int. Ed. 2015; 54: 7256
5j Yokoi H, Hiraoka Y, Hiroto S, Sakamaki D, Seki S, Shinokubo H. Nat. Commun. 2015; 6: 8215
5k Wang S, Li X, Hou X, Sun Y, Shao X. Chem. Commun. 2016; 52: 14486
5l Hou X, Zhu Y, Qin Y, Chen L, Li X, Zhang H.-L, Xu W, Zhu D, Shao X. Chem. Commun. 2017; 53: 1546
5m Furukawa S, Suda Y, Kobayashi J, Kawashima T, Tada T, Fujii S, Kiguchi M, Saito M. J. Am. Chem. Soc. 2017; 139: 5787
5n Kaewmati P, Tan Q, Higashibayashi S, Yakiyama Y, Sakurai H. Chem. Lett. 2017; 46: 146
5o Tan Q, Zhou D, Zhang T, Liu B, Xu B. Chem. Commun. 2017; 53: 10279
5p Tan Q, Kaewmati P, Higashibayashi S, Kawano M, Yakiyama Y, Sakurai H. Bull. Chem. Soc. Jpn. 2018; 91: 531
5q Wang S, Yan C, Shang J, Wang W, Yuan C, Zhang H.-L, Shao X. Angew. Chem. Int. Ed. 2019; 58: 3819

6a Seiders TJ, Elliott EL, Grube GH, Siegel JS. J. Am. Chem. Soc. 1999; 121: 7804
6b Sygula A, Rabideau PW. J. Am. Chem. Soc. 2000; 122: 6323
6c Xu G, Sygula A, Marcinow Z, Rabideau PW. Tetrahedron Lett. 2000; 41: 9931
6d Grube GH, Elliott EL, Steffens RJ, Jones CS, Baldridge KK, Siegel JS. Org. Lett. 2003; 5: 713
6e Wu Y.-T, Bandera D, Maag R, Linden A, Baldridge KK, Siegel JS. J. Am. Chem. Soc. 2008; 130: 10729
6f Baldridge KK, Hardcastle KI, Seiders TJ, Siegel JS. Org. Biomol. Chem. 2010; 8: 53
6g Pogoreltsev A, Solel E, Pappo D, Keinan E. Chem. Commun. 2012; 48: 5425

Functionalization at benzylic carbons:

7a Sakurai H, Daiko T, Hirao T. Science 2003; 301: 1878
7b Sakurai H, Daiko T, Sakane H, Amaya T, Hirao T. J. Am. Chem. Soc. 2005; 127: 11580
7c Amaya T, Nakata T, Hirao T. J. Am. Chem. Soc. 2009; 131: 10810
7d Amaya T, Hifumi M, Okada M, Shimizu Y, Moriuchi T, Segawa K, Ando Y, Hirao T. J. Org. Chem. 2011; 76: 8049
7e Amaya T, Mori K, Wu H.-L, Ishida S, Nakamura J, Murata K, Hirao T. Chem. Commun. 2007; 1902
7f Higashibayashi S, Nasir Baig RB, Morita Y, Sakurai H. Chem. Lett. 2012; 41: 84
7g Higashibayashi S, Tsuruoka R, Soujanya Y, Purushotham U, Sastry GN, Seki S, Ishikawa T, Toyota S, Sakurai H. Bull. Chem. Soc. Jpn. 2012; 85: 450
7h Schmidt BM, Topolinski B, Higashibayashi S, Kojima T, Kawano M, Lentz D, Sakurai H. Chem. Eur. J. 2013; 19: 3282
7i Higashibayashi S, Onogi S, Srivastava HK, Sastry GN, Wu Y.-T, Sakurai H. Angew. Chem. Int. Ed. 2013; 52: 7314
7j Amaya T, Ito T, Hirao T. Eur. J. Org. Chem. 2014; 3531
7k Amaya T, Ito T, Katoh S, Hirao T. Tetrahedron 2015; 71: 5906
7l Yakiyama Y, Wang Y, Hatano S, Abe M, Sakurai H. Chem. Asian J. 2019; 14: 1844

Functionalization at aromatic carbons:

8a Shrestha BB, Karanjit S, Panda G, Higashibayashi S, Sakurai H. Chem. Lett. 2013; 42: 386
8b Amaya T, Kobayashi K, Hirao T. Asian J. Org. Chem. 2013; 2: 642
8c Shrestha BB, Higashibayashi S, Sakurai H. Beilstein J. Org. Chem. 2014; 10: 841
8d Shrestha BB, Karanjit S, Higashibayashi S, Amaya T, Hirao T, Sakurai H. Asian J. Org. Chem. 2015; 4: 62
8e Ngamsomprasert N, Panda G, Higashibayashi S, Sakurai H. J. Org. Chem. 2016; 81: 11978
8f Ngamsomprasert N, Yakiyama Y, Sakurai H. Chem. Lett. 2017; 46: 446
8g Toda H, Yakiyama Y, Shoji Y, Ishiwari F, Fukushima T, Sakurai H. Chem. Lett. 2017; 46: 1368
8h Shoji Y, Kajitani T, Ishiwari F, Ding Q, Sato H, Anetai H, Akutagawa T, Sakurai H, Fukushima T. Chem. Sci. 2017; 8: 8405
8i Hisaki I, Toda H, Sato H, Tohnai N, Sakurai H. Angew. Chem. Int. Ed. 2017; 56: 15294

9a Ueda T, Konishi H, Manabe K. Org. Lett. 2012; 14: 3100
9b Fujihara T, Hosoki T, Katafuchi Y, Iwai T, Terao J, Tsuji Y. Chem. Commun. 2012; 48: 8012

10 Mebs S, Weber M, Luger P, Schmidt BM, Sakurai H, Higashibayashi S, Onogi S, Lentz D. Org. Biomol. Chem. 2012; 10: 2218
11 Armaković S, Armaković SJ, Šetrajčić JP, Šetrajčić IJ. Chem. Phys. Lett. 2013; 578: 156
12 DFT/TD-DFT calculations of 5 for assignment of the transitions corresponding to UV absorption bands did not converge, probably due to the flexibility of the phenoxycarbonyl groups.
13 Zanello P, Fedi S, Fabrizi de Biani F, Giorgi G, Amaya T, Sakane H, Hirao T. Dalton Trans. 2009; 9192

Zusatzmaterial

Supporting Information