Volume 47, Issue 11 pp. 2067-2069

Communication

Highly Selective Photomediated 1,4-Radical Addition to o-Quinones Controlled by a Self-Assembled Cage^†

Takumi Yamaguchi

Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan, Fax: (+81) 3-5841-7257

Search for more papers by this author

Makoto Fujita Prof. Dr.,

Makoto Fujita Prof. Dr.

[email protected]

Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan, Fax: (+81) 3-5841-7257

Search for more papers by this author

Takumi Yamaguchi,

Takumi Yamaguchi

Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan, Fax: (+81) 3-5841-7257

Search for more papers by this author

Makoto Fujita Prof. Dr.,

Makoto Fujita Prof. Dr.

[email protected]

Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan, Fax: (+81) 3-5841-7257

Search for more papers by this author

First published: 22 February 2008

https://doi.org/10.1002/anie.200705139

Citations: 123

^†

This research was supported by KAKENHI provided by MEXT/JSPS (for M.F., Grant No. 19205012).

Share a link

Email
Wechat
Bluesky

Graphical Abstract

Cavity control: A highly selective 1,4-addition reaction of a toluene derivative to o-quinones proceeds efficiently within a self-assembled coordination cage (see scheme). The cage accelerates the formation of the 1,4-adduct but suppresses all other reaction pathways that are normally favorable in the absence of the cage.

Supporting Information

References

1J. Rétey, Angew. Chem. 1990, 102, 373–379;
10.1002/ange.19901020407
CAS Google Scholar
Angew. Chem. Int. Ed. Engl. 1990, 29, 355–361.
10.1002/anie.199003551
Web of Science® Google Scholar
2W. Buckel, B. T. Golding, FEMS Microbiol. Rev. 1998, 22, 523–541.
10.1111/j.1574-6976.1998.tb00385.x
CAS Web of Science® Google Scholar
3
3aM. Yoshizawa, M. Fujita, Pure Appl. Chem. 2005, 77, 1107–1112;
10.1351/pac200577071107
CAS Web of Science® Google Scholar
3bM. Yoshizawa, M. Tamura, M. Fujita, Science 2006, 312, 251–254;
10.1126/science.1124985
CAS PubMed Web of Science® Google Scholar
3cT. Furusawa, M. Kawano, M. Fujita, Angew. Chem. 2007, 119, 5819–5821;
10.1002/ange.200701250
Google Scholar
Angew. Chem. Int. Ed. 2007, 46, 5717–5719;
10.1002/anie.200701250
CAS PubMed Web of Science® Google Scholar
3dY. Nishioka, T. Yamaguchi, M. Yoshizawa, M. Fujita, J. Am. Chem. Soc. 2007, 129, 7000–7001.
10.1021/ja071591x
CAS PubMed Web of Science® Google Scholar
4Reactions within artificial hosts:
Google Scholar
4aD. M. Vriezema, M. C. Aragonès, J. A. A. W. Elemans, J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, Chem. Rev. 2005, 105, 1445–1489;
10.1021/cr0300688
CAS PubMed Web of Science® Google Scholar
4bL. S. Kaanumalle, C. L. D. Gibb, B. C. Gibb, V. Ramamurthy, Org. Biomol. Chem. 2007, 5, 236–238;
10.1039/B617022F
CAS PubMed Web of Science® Google Scholar
4cA. Natarajan, L. S. Kaanumalle, S. Jockusch, C. L. D. Gibb, B. C. Gibb, N. J. Turro, V. Ramamurthy, J. Am. Chem. Soc. 2007, 129, 4132–4133;
10.1021/ja070086x
CAS PubMed Web of Science® Google Scholar
4dM. D. Pluth, R. G. Bergman, K. N. Raymond, Science 2007, 316, 85–88.
10.1126/science.1138748
CAS PubMed Web of Science® Google Scholar
5Photoreactions of o-quinones:
Google Scholar
5aM. B. Rubin, J. Org. Chem. 1963, 28, 1949–1952;
10.1021/jo01043a001
CAS Web of Science® Google Scholar
5bM. B. Rubin, P. Zwitkowits, J. Org. Chem. 1964, 29, 2362–2368;
10.1021/jo01031a062
CAS Web of Science® Google Scholar
5cM. B. Rubin, P. Zwitkowits, Tetrahedron Lett. 1965, 6, 2453–2457;
10.1016/S0040-4039(01)84006-5
Google Scholar
5dK. Maruyama, M. Muraoka, Y. Naruta, J. Org. Chem. 1981, 46, 983–989;
10.1021/jo00318a026
CAS Web of Science® Google Scholar
5eC. Tintel, J. Terheijden, J. Lugtenburg, J. Cornelisse, Tetrahedron Lett. 1987, 28, 2057–2060.
10.1016/S0040-4039(00)96044-1
CAS Web of Science® Google Scholar
6T. Kusukawa, M. Yoshizawa, M. Fujita, Angew. Chem. 2001, 113, 1931–1936;
10.1002/1521-3757(20010518)113:10<1931::AID-ANGE1931>3.0.CO;2-X
Google Scholar
Angew. Chem. Int. Ed. 2001, 40, 1879–1884.
10.1002/1521-3773(20010518)40:10<1879::AID-ANIE1879>3.0.CO;2-I
CAS PubMed Web of Science® Google Scholar
7M. Yoshizawa, M. Tamura, M. Fujita, J. Am. Chem. Soc. 2004, 126, 6846–6847.
10.1021/ja048860t
CAS PubMed Web of Science® Google Scholar
8Crystallographic data for 1 b⋅(2⋅3): tetragonal, space group P4₁2₁2, T=80(2) K, a=b=28.996(3) Å, c=30.280(6) Å, V=25459(6) Å³, Z=4, ρ_calcd=1.142 Mg m⁻³, R₁=0.1090, wR₂=0.3619. CCDC-666355 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
Google Scholar
9E. T. Mack, A. B. Carle, J. T.-M. Liang, W. Coyle, R. M. Wilson, J. Am. Chem. Soc. 2004, 126, 15324–15325.
10.1021/ja0473788
CAS PubMed Web of Science® Google Scholar

Citing Literature

Volume47, Issue11

February 28, 2008

Pages 2067-2069

Highly Selective Photomediated 1,4-Radical Addition to o-Quinones Controlled by a Self-Assembled Cage^†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Highly Selective Photomediated 1,4-Radical Addition to o-Quinones Controlled by a Self-Assembled Cage†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Related

Information

Highly Selective Photomediated 1,4-Radical Addition to o-Quinones Controlled by a Self-Assembled Cage^†