Highly selective sequential addition and cyclization reactions involving diphenyl diselenide, an alkyne, and alkenes under visible-light irradiation

Angewandte Chemie - International Edition

Volumn 42, Issue 30, 2003, Pages 3490-3493

  Tsuchii, Kaname ^a   Doi, Mikio ^b   Hirao, Toshikazu ^b   Ogawa, Akiya ^a  

^a NARA WOMEN'S UNIVERSITY   (Japan)

^b NONE

Author keywords

Alkenes; Alkynes; Cyclizations; Domino reactions; Radicals

Indexed keywords

ADDITION REACTIONS; CARBON; ELECTRONS; REACTION KINETICS; SUBSTITUTION REACTIONS;

CYCLOPENTANES;

OLEFINS;

ALKENE; ALKYNE;

ARTICLE; CHEMICAL REACTION; COUPLING FACTOR; CYCLIZATION; ELECTRON TRANSPORT; IRRADIATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0041529854     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250790     Document Type: Article

References (23)

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10. The stereochemistry of the sequential addition and cyclization products was determined by NOE experiments (see Supporting Information).
11. E. Lee, C. U. Hur, Y. H. Rhee, Y. C. Park, S. Y. Kim, J. Chem. Soc. Chem. Commun. 1993, 1466-1468.
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14. 2 to alkynes, see: a) T. G. Back, M. V. Krishna, J. Org. Chem. 1988, 53, 2533-2536; b) A. Ogawa, H. Yokoyama, K. Yokoyama, T. Masawaki, N. Kambe, N. Sonoda, J. Org. Chem. 1991, 56, 5721-5723; c) A. Ogawa, N. Takami, M. Sekiguchi, H. Yokoyama, H. Kuniyasu, I. Ryu, N. Sonoda, Chem. Lett. 1991, 2241-2242.
15. 2 to alkynes, see: a) T. G. Back, M. V. Krishna, J. Org. Chem. 1988, 53, 2533-2536; b) A. Ogawa, H. Yokoyama, K. Yokoyama, T. Masawaki, N. Kambe, N. Sonoda, J. Org. Chem. 1991, 56, 5721-5723; c) A. Ogawa, N. Takami, M. Sekiguchi, H. Yokoyama, H. Kuniyasu, I. Ryu, N. Sonoda, Chem. Lett. 1991, 2241-2242.
16. 2 to alkynes, see: a) T. G. Back, M. V. Krishna, J. Org. Chem. 1988, 53, 2533-2536; b) A. Ogawa, H. Yokoyama, K. Yokoyama, T. Masawaki, N. Kambe, N. Sonoda, J. Org. Chem. 1991, 56, 5721-5723; c) A. Ogawa, N. Takami, M. Sekiguchi, H. Yokoyama, H. Kuniyasu, I. Ryu, N. Sonoda, Chem. Lett. 1991, 2241-2242.
17. In general, vinyl radicals are believed to be a stereoisomeric mixture of σ radicals that are in rapid equilibrium: a) R. W. Fessenden, R. H. Schuler, J. Chem. Phys. 1963, 39, 2147-2195. In contrast, α-aryl-substituted vinylic radicals are thought to be π radicals: b) L. A. Singer, J. Chen, Tetrahedron Lett. 1969, 10, 4849-4854. The corresponding radical species derived from ethyl propiolate is thought to be a vinylic π radical: c) C. Galli, A. Guarnieri, H. Koch, P. Mencarelli, Z. Rappoport, J. Org. Chem. 1997, 62, 4072-4077; d) H. Rubin, H. Fischer, Helv. Chim. Acta 1996, 79, 1670-1682; e) J. O. Metzger, M. Blumenstein, Chem. Ber. 1993, 126, 2493-2499.
18. In general, vinyl radicals are believed to be a stereoisomeric mixture of σ radicals that are in rapid equilibrium: a) R. W. Fessenden, R. H. Schuler, J. Chem. Phys. 1963, 39, 2147-2195. In contrast, α-aryl-substituted vinylic radicals are thought to be π radicals: b) L. A. Singer, J. Chen, Tetrahedron Lett. 1969, 10, 4849-4854. The corresponding radical species derived from ethyl propiolate is thought to be a vinylic π radical: c) C. Galli, A. Guarnieri, H. Koch, P. Mencarelli, Z. Rappoport, J. Org. Chem. 1997, 62, 4072-4077; d) H. Rubin, H. Fischer, Helv. Chim. Acta 1996, 79, 1670-1682; e) J. O. Metzger, M. Blumenstein, Chem. Ber. 1993, 126, 2493-2499.
19. In general, vinyl radicals are believed to be a stereoisomeric mixture of σ radicals that are in rapid equilibrium: a) R. W. Fessenden, R. H. Schuler, J. Chem. Phys. 1963, 39, 2147-2195. In contrast, α-aryl-substituted vinylic radicals are thought to be π radicals: b) L. A. Singer, J. Chen, Tetrahedron Lett. 1969, 10, 4849-4854. The corresponding radical species derived from ethyl propiolate is thought to be a vinylic π radical: c) C. Galli, A. Guarnieri, H. Koch, P. Mencarelli, Z. Rappoport, J. Org. Chem. 1997, 62, 4072-4077; d) H. Rubin, H. Fischer, Helv. Chim. Acta 1996, 79, 1670-1682; e) J. O. Metzger, M. Blumenstein, Chem. Ber. 1993, 126, 2493-2499.
20. In general, vinyl radicals are believed to be a stereoisomeric mixture of σ radicals that are in rapid equilibrium: a) R. W. Fessenden, R. H. Schuler, J. Chem. Phys. 1963, 39, 2147-2195. In contrast, α-aryl-substituted vinylic radicals are thought to be π radicals: b) L. A. Singer, J. Chen, Tetrahedron Lett. 1969, 10, 4849-4854. The corresponding radical species derived from ethyl propiolate is thought to be a vinylic π radical: c) C. Galli, A. Guarnieri, H. Koch, P. Mencarelli, Z. Rappoport, J. Org. Chem. 1997, 62, 4072-4077; d) H. Rubin, H. Fischer, Helv. Chim. Acta 1996, 79, 1670-1682; e) J. O. Metzger, M. Blumenstein, Chem. Ber. 1993, 126, 2493-2499.
21. In general, vinyl radicals are believed to be a stereoisomeric mixture of σ radicals that are in rapid equilibrium: a) R. W. Fessenden, R. H. Schuler, J. Chem. Phys. 1963, 39, 2147-2195. In contrast, α-aryl-substituted vinylic radicals are thought to be π radicals: b) L. A. Singer, J. Chen, Tetrahedron Lett. 1969, 10, 4849-4854. The corresponding radical species derived from ethyl propiolate is thought to be a vinylic π radical: c) C. Galli, A. Guarnieri, H. Koch, P. Mencarelli, Z. Rappoport, J. Org. Chem. 1997, 62, 4072-4077; d) H. Rubin, H. Fischer, Helv. Chim. Acta 1996, 79, 1670-1682; e) J. O. Metzger, M. Blumenstein, Chem. Ber. 1993, 126, 2493-2499.
22. The stereochemistry of the four-component coupling products was determined by NOE experiments (see Supporting Information).
23. 2 with 1 was formed as a by-product.