Rhodium
(Chief Bee)
04-25-03 22:52
No 429395
      Photophtalimidation of styrenes to PEAs
(Rated as: excellent)
    

Photoinduced SET phthalimidation of unactivated double bonds and its application to the synthesis of protected phenethylamines
Tetrahedron 59(16), 2913-2919 (2003) (../rhodium/pdf /photophtalimidation.pdf)
DOI:10.1016/S0040-4020(03)00343-0



Abstract

Phthalimide, in equilibrium with its conjugate base, adds photochemically to cyclohexene and aryl-substituted alkenes (photophthalimidation). The efficient, predictable regioselective photophthalimidation of styrenes constitutes a synthetically useful process for the preparation of N-phenethyl-phthalimides. A possible mechanism for the photophthalimidation involves the nucleophilic attack of phthalimide anion on the alkene cation-radical generated by single electron transfer to excited phthalimide.
 
 
 
 
    Rhodium
(Chief Bee)
09-26-03 01:06
No 461084
      Photoamination References
(Rated as: good read)
    

Photoamination References (found by jim at http://kb3.chem.miyazaki-u.ac.jp/y1ken/pac.html )

1) Synthetic Application of Photochemical Electron Transfer to Direct Amination of Arenes  by Ammonia and Primary Amines, M. Yasuda, T. Yamashita, T. Matsumoto, K. Shima, and C. Pac, J. Org. Chem., 50, 3667-3669 (1985)

2) Direct Photoamination of Arenes with Ammonia and Primary Amines in the Presence of Electron Acceptors, M. Yasuda, T. Yamashita, K. Shima, and C. Pac, J. Org. Chem., 52, 753 (1987)

3) Mechanisms for Direct Photoamination of Arenes with Ammonia and Amines in the Presence of m-Dicyanobenzene, M. Yasuda, Y. Matsuzaki, K. Shima, and C. Pac, J. Chem. Soc. Perkin Trans. 2, 1988, 745

4) Synthesis of Isoquinoline precursors by Photoamination of Stilbenes with Bifunctional Alkylamines, M. Yasuda, J. Kubo, and K. Shima, Heterocycles, 31, 1007 (1990)

5) Photoinduced Nucleophilic Addition of Ammonia and Alkylamines to Aryl-Substituted Alkenes in the Presence of p-Dicyanobenzene, T. Yamashita, K. Shiomori, M. Yasuda, and K. Shima, Bull. Chem. Soc. Jpn., 64, 366 (1991)

6) Regiochemistry on Photoamination of Stilbene Derivatives with Ammonia via Electron Transfer, M. Yasuda, T. Isami, J. Kubo, M. Mizutani, T. Yamashita, and K. Shima, J. Org. Chem., 57, 1351 (1992)

7) Stereochemical Studies on the Amination of Arenes with Ammonia and Alkylamines via Photochemical Electron Transfer, M. Yasuda, K. Shiomori, S. Hamasuna, K. Shima, and T. Yamashita, J. Chem. Soc. Perkin Trans. 2, 1992, 305

8) Application of Photoamination to Synthesis of Benzylisoquinoline, Aporphins, and Isopavines, M. Yasuda, S. Hamasuna, K. Yamano, J. Kubo, and K. Shima, Heterocycles, 34, 965-977 (1992)

9) A Convenient Method for Synthesis of 1-Amino-2-tetralones by Photoamination of 2-Alkoxynaphthalenes with Alkylamines, T. Yamashita, K. Yamano, M. Yasuda, and K. Shima, Chem. Lett., 1993, 627-630

10) Synthesis of Phenylethylamine Moiety by Photoamination of Styrene Derivatives with Ammonia, T. Yamashita, M. Yasuda, T. Isami, S. Nakazono, K. Tanabe, and K. Shima, Tetrahedron Lett., 34, 5131-5134 (1993)

11) Photoamination of 2-Alkoxynaphthalenes with Alkylamines via Electron Transfer and Its Application to Synthesis of 1-Alkylamino-2-tetralones, T. Yamashita, K. Tanabe, K. Yamano, M. Yasuda, and K. Shima, Bull. Chem. Soc. Jpn., 67, 246-250 (1994).

12) Amination of o-Alkenylphenols with Alkylamines via Photoinduced Proton Transfer, M. Yasuda, T. Sone, K. Tanabe, and K. Shima, Chem. Lett., 1994, 453-456

13) Regiochemistry on Photoamination of Methoxy-Substituted Phenanthrene via Electron Transfer, M. Yasuda, Y. Watanabe, K. Tanabe, and K. Shima, J. Photochem. Photobiol. A: Chem., 79, 61-65 (1994)

14) Photoinduced Nucleophilic Addition of Ammonia and Alkylamines to Methoxy- Substituted Styrene Derivatives, T. Yamashita, M. Yasuda, T. Isami, K. Tanabe, and K. Shima, Tetrahedron, 50, 9275-9286 (1994)

15) Photochemical Reactions of o-Alkenylphenols and 1-Alkenyl-2-naphthol with Alkylamines: Amination via Photoinduced Proton transfer, M. Yasuda, T. Sone, K. Tanabe, and K. Shima, J. Chem. Soc. Perkin Trans. 1, 1995, 459-464.

16) New Synthetic Route to Dibenzo[a,d]cycloheptenimines through Photoamination of 5-Alkoxy- and 5-Hydroxysibenzo[a,d]cycloheptenes Follwed by Trasannular Reaction with Acetic Acid, M. Yasuda, T. Wakisaka, R. Kojima, K. Tanabe,  and K. Shima, Bull. Chem. Soc. Jpn., 1995, 68, 3169-3173

17) Regioselective 1,4-Addition of Ammonia to 1-Aryl-1,3-alkadienes and 1,4-Diaryl-1,3-butadienes via Photoinduced Electron Transfer, R. Kojima, T. Yamashita, K. Tanabe, T. Shiragami, M. Yasuda, and K. Shima, J. Chem. Soc. Perkin Trans. 1, 1997, 217-222

18) Intramolecular Cyclization of 1,2-Distyrylbenzene via Cation Radical Generated by Photoinduced Photoinduced Electron Transfer, R. Kojima, T. Shiragami, K. Shima, M. Yasuda, and T. Majima, Chem. Lett.,  1997, 1241-1242

19) Photoamination of Alkenylnaphthalene with Ammonia via Electron Transfer, M. Yasuda, R. Kojima, R. Ohira, T. Shiragami, and K. Shima, Bull. Chem. Soc. Jpn., 71, 1655-1660 (1998)

20) Photoamination of 1,2-Diarylcyclopropanes Using 2,2'-Dialkoxy-1,1'-binaphthalene as Redox-Photosensitizer, M. Yasuda, R. Kojima, H. Tsutsui, L. A. Watanabe, J. Hobo, T. Yamashita, T. Shiragami, K. Shima Chem. Lett.,  1999, 1269-1270

21) Remarkable Effect of Surfactant on Flavin Photochemistry.  Monomerization of Thymine   Cyclobutane Dimers Photosensitized by Flavins in the Presence of SDS in Aqueous Solution, M. Yasuda, T. Nakazono, T. Hamasaki, Y. Nishinaka, N. Nakamura, C. Pac,  and K. Shima, Chem. Lett., 1995, 563-564.

22) Photochemistry of Flavins in Micelles: Specific Effects of Anionic Surfactants on the Monomerization of Thymine Cyclobutane Dimers Photosensitized by Tetra-O-acylriboflavins, M. Yasuda, Y. Nishinaka, T. Nakazono, T. Hamasaki, N. Nakamura, T. Shiragami, C. Pac, and  K. Shima,   Photochem. Photobiol.., 1998, 67, 192- 97.

23) Photoreactions of 1-Cyanonaphthalene with Indene in Various Solvents, M. Yasuda, C. Pac, and H. Sakurai, Bull. Chem. Soc. Jpn., 53, 502 (1980)

24) Direct Photocyanation of Arenes with Sodium Cyanide in the Presence of Electron Acceptors, M. Yasuda, C. Pac, and H. Sakurai, J. Chem. Soc., Perkin Trans. 1, 1981, 746

25) Photo-Birch Reduction of Arenes with Sodium Borohydride in the Presence of Dicyanobenzene, M. Yasuda, C. Pac, and H. Sakurai, J. Org. Chem., 46, 788 (1981)

26) The Photoreactions of Anthracene with  Some Selected Tertiary Aromatic Amines in Polar Media, M. Yasuda, C. Pac, and H. Sakurai, Bull. Chem. Soc. Jpn., 54, 2352 (1981)

27) Ru(bpy)32+-Mediated Photoreduction of Olefins with 1-Benzyl-1,4-dihydronicotinamide: A Mechanistic Probe for Electron-Transfer Reaction of NAD(P)H-Model Compounds, C. Pac, M. Ihama, M. Yasuda, Y. Miyauchi, and H. Sakurai, J. Am. Chem. Soc., 103, 6495 (1981)

28) Ru(bpy)32+-Photosensitized Reactions of 1-Benzyl-1,4-dihydronicotinamide with Ary-Substituted Enones, Derivatives of Methyl Cinnamate, and Substituted Cinnamonitriles: Electron-Transfer Mechanism and Structure-Reactivity Relationships, C. Pac, Y. Miyauchi, O. Ishitani, M. Ihama, M. Yasuda, and H. Sakurai, J. Org. Chem., 49, 26 (1984)

29) Direct Phosphonation of Naphthalene and Phenanthrene with Trialkyl Phosphites via Photochemical Electron Transfer, M. Yasuda, T. Yamashita, and K. Shima, Bull. Chem. Soc., Jpn., 63, 938 (1990)

30) A Novel Type of Cyanomethylation Reaction of Diarylethenes with Acetonitrile Photosensitized by Benzophenone in the Presence of t-Butylamine, T. Yamashita, M. Yasuda, M. Watanabe, R. Kojima, K. Tanabe, and K. Shima,        J. Org. Chem., 1996, 64, 6438-6441

31) Benzophenone-Photosensitized Alkylation of Arylalkenes with Acetone, Dimethyl Sulfoxide, and their Related Compounds in the Presence of tert-Butylamine, T. Yamashita, M. Watanabe, R. Kojima, T. Shiragami, K. Shima, and M. Yasuda, J. Photochem. Photobiol. A: Chem., 118, 165-171 (1998).

32) Solvent Effects on Fluorescence Quenching and Photoreactions of Naphthalene-Olefin and Furan Systems. Qualitative Consideration on Electronic Structures and Reactivities of Nonemissive Exciplexes, C. Pac, M. Yasuda, K. Shima, and H. Sakurai, Bull. Chem. Soc, Jpn., 55, 1605 (1982)

33) Salt-Induced Photoamination of Arenes by Aliphatic Amines via Arene/p-Dicyanobenzene Exciplexes. A Mechanism for Salt Effects on Charge Separation of Exciplexes, M. Yasuda, Y. Matsuzaki, T. Yamashita, and K. Shima, Chem. Lett., 1989, 551

34) Salt-Induced Photoamination of Arenes by Aliphatic Amines via Arene/p-Dicyanobenzene Exciplexes. A Mechanism for Salt Effects on Charge Separation of Exciplexes, M. Yasuda, Y. Matsuzaki, T. Yamashita, and K. Shima, Chem. Lett., 1989, 551

35) [Unreadable - Japanese Reference]

36) Unusual Effects of Acetate Ion on Photosensitized Oxygenation of Naphthalene Derivatives via Electron Transfer, T.
Yamashita, T. Tsurusako, M. Yasuda, and  K. Shima, Chem. Lett., 1991, 1487

37) Electron-Trsansfer Photosensitized Oxygenation of Stilbene and Naphthalene Derivatives in the Presence of Acetate Ion. Controlling the Reaction of the Cation Radicals by Weak-Nucleophilic Salts, T. Yamashita, T. Tsurusako, N. Nakamura, M. Yasuda, and K. Shima, Bull, Chem. Soc. Jpn., 66, 857-862 (1993)

38) Fluorescence Study on Polar Intramolecular Exciplexes of 9-(Phenanthroxy)alkyl p-Cyanobenzoates, M. Yasuda, G. Kuwamura, and K. Shima, J. Photochem. Photobiol. A: Chem., 86, 127-131 (1995).

39) Solvent Parameter Based on the Exciplex Emission of (2-Naphthoxy)polyalkyl p-Cyanobenzoates, M. Yasuda, Y. Kawahito, K. Sasano, Y. Andou, T. Shiragami, and  K. Shima, Photochem. Photobiol.. A: Chem., 121, 149-155 (1999).

40) Photosensitized Ring-Cleavage Reactions of 2,2-Diaryloxetanes by Aromatic Nitriles, K. Nakabayashi, J. Kojima, K. Tanabe, M. Yasuda, and K. Shima, Bull. Chem. Soc. Jpn., 62, 96 (1989).

41) Photochemical Ring-Cleavage Reactions of 2,2-Diaryloxetanes in the Presence of Electron Donor, K. Nakabayashi, S. Fujimura, M. Yasuda, and K. Shima, Bull. Chem. Soc. Jpn., 62, 2733 (1989)

42) Ring-Splitting Reaction of 2,2-Diarylthietane by Electron-Transfer Photosensitization of 9,10-Dicyanoanthracene, K. Shima, A. Sazaki, K. Nakabayashi, and M. Yasuda, Bull. Chem. Soc. Jpn.,  65, 1472-1474 (1992)

43) Efficient Cross-Photocycloadditions of Vinylcoumarins to Olefins, M. Yasuda, T. Kishi, C. Goto, H. Satoda, K. Nakabayashi, T. Minami, and K. Shima, Tetrahedron Lett., 33, 6465-6468 (1992)

44) Cycloreversion of Aryl-Substituted Cyclobutene by Direct Photolysis and Pulse Radiolysis, K. Nakabayashi, Y. Tahara, M. Yasuda, K. Shima, and S. Takamuku, Bull. Chem. Soc. Jpn., 66, 698-702 (1993).

45) Mechanistic Studies for Cross-Photocycloadditions of 3-Vinylcoumarin Derivativres to Electron-Rich Olefins, M. Yasuda, T. Kishi, C. Goto, H. Satoda, and K. Shima, J. Photochem. Photobiol. A: Chem., 76, 61-67 (1993)

46) Cycloreversion of 1-(1-Naphtyl)-5-phenylbicyclo[3.2.0]hept-6-ene to 1-(1-Naphtyl)- 4-phenyl-1,3-cycloheptadiene by Triplet Sensitization and Direc Irradiation, K. Nakabayashi, J. Arimura, M. Yasuda,  K. Shima, and S. Takamuku, Bull. Chem. Soc. Jpn., 1996, 69, 1313-1317.

47) Reductant-induced Homolysis of the Thallium-Carbon Bond: Novel Oxygenation of Alkylthallium (III) Compounds with Ascorbic Acid, H. Kurosawa and M. Yasuda, J. Chem. Soc. Chem. Comm., 1978, 716

48) Homolysis of the Tl-C Bond in Hydrodethallation of Alkylthallium (III) Compounds with N-Benzyl-1,4-dihydronicotinamide, H. Kurosawa, H. Okada, and M. Yasuda, Tetrahedron Lett., 21. 959 (1980)

49) Acid-Catalysed Rearangements of [4.3.2]- and [3.3.3]Propellanes Tricyclo[4.3.2.01,5]- undecanes, and Tricyclo[6.3.0.01,5]undecanes, K. Kakiuchi, M. Ue, I. Wakaki, Y. Tobe, Y. Odaira, M. Yasuda, and K. Shima, J. Org. Chem., 51, 281 (1986)

50) Solvolytic Rearrangement of 5,6-Polymethylenebicyclo[4.2.0]octan-2-ol Derivatives to Functionalized Polymethylenebicyclo[3.2.1]- and [3.3.0]octanes, M. Ue, T. Nagashima, M. Kinugawa, K. Kakiuchi, Y. Tobe, Y. Odaira, M.Yasuda, and K. Shima, Chem. Lett., 1988, 1521

51) Novel Rearrangement of 5,6-Disubstituted Bicyclo[4.2.0]octan-2-ones with AlCl3. Application  to Total Synthesis of ()-5-Oxosilphiperfol-6-ene and ()-Silphiperfol-6-ene, K. Kakiuchi, M. Ue, H. Tsukahara, T. Shimizu, T. Miyao, Y. Tobe, Y. Odaira, M. Yasuda,  and K. Shima, J. Am. Chem. Soc., 111, 3707 (1989).

52) Molecular Structures of Diarylcyclobutanes Associated with Reactivities in Ring-CleavageReactions: Implications of Conformationally Controlled Through-Bond Coupling, K. Shima, J. Kimura, K. Yoshida, M. Yasuda, K.Imada, and C. Pac, Bull. Chem. Soc. Jpn., 62, 1934 (1989).

53) Thermal Ring-Splitting Reactions of Diarylcyclobutanes: Significance of Steric Effects on  Orbital Interactions in Transition States and Biradical Intermediates, M. Yasuda, K. Yoshida, K. Shima, C. Pac, and S. Yanagida, Bull. Chem. Soc. Jpn., 62, 1943 (1989)

54) Cycloreversion of 1,4-Diphenylbicyclo[3.2.0]hept-2-ene under Triplet Sensitization. An Adiabatic Process on the Triplet Surface, K. Nakabayashi, W. Fukumoto, M. Yasuda, K. Shima, and S. Takamuku, Chem. Lett., 1992, 803-806

55) Photochemical Reactions of 1,4-Dicyanonaphthalene with Allylic Silanes: Control of Reaction Modes by Use of Solvent and Additive Effects, K. Mizuno, K. Terasaka, T. Nishiyama, M. Yasuda, K. Shima, T. Tamai, and Y. Otsuji, Tetrahedron, 48, 9673-9686 (1992)

56) Dehydroamination Reactions of 9-Amino-9,10-dihydrophenanthrene and Related Compounds by Thermolysis, M. Yasuda, T. Harada, Y. Ansho, and K. Shima, Bull. Chem. Soc. Jpn., 66, 1451-1455 (1993)

57) Highly Twisted tert-Butoxycarbonyl in Hexa-tert-Butyl Benzenehexacarboxylate.  The Structural Origin of Steric Hindrance-Induced Dual Fluorescence, M. Yasuda, G. Kuwamura, T. Nakazono, K. Shima, Y. Inoue, N. Yamasaki, and A. Tai, Bull. Chem. Soc. Jpn., 67, 505-510 (1994).

58) A Carbon-Centered Radical as a Reaction Species in the DNA Strand-Breakage by D-Glucosamine, T. Yamaguchi, N. Kashige, S. Matsumoto, K. Satoh, M. Yasuda, and K. Watanabe, Biol.Pham. Bull., 1998,  21, 205-209.


Reviews

1) Amination of Electron-Rich Substrates via Photoinduced Electron Transfer: Mechanism and Synthetic Application, M. Yasuda and K. Shima, Reviews on Heteroatom Chemistry,  4, 27 (1991)

2) Application of Photoinduced Nucleophilic Addition Reaction to Organic Synthesis, M. Yasuda and K. Shima,Trends in Organic Chemistry,  4, 291-302 (1993)

3) Photoamination Directed toward the Synthesis of Heterocyclic Compounds, M. Yasuda, T. Yamashita, R. Kojima, and K. Shima, Heterocycles,  43, 2513-2522 (1996)

4) Photoamination via Electron Transfer, M. Yasuda, T. Yamashita, T. Shiragami, and K. Shima, Recent Reasearch Deveolpment in Photochemistry & Photobiology,  3 65-76 (1999)