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DOI: 10.1055/s-2006-958949
The Photo-Dehydro-Diels-Alder (PDDA) Reaction - A Powerful Method for the Preparation of Biaryls
Publication History
Publication Date:
14 December 2006 (online)

Abstract
The photochemically initiated dehydro-Diels-Alder (PDDA) reaction is an efficient and versatile method for the preparation of biaryls. The ring closure may take place both inter- and intramolecularly, of which the intramolecular variant is more productive from the preparative point of view. A variety of linkers can be employed to connect the ynone moiety, which acts as the chromophore, with another acetylene group, thus allowing large structural versatility. Principles influencing the site selectivity of the PDDA reaction will also be discussed here.
Key words
photochemistry - biaryls - alkynes - photo-dehydro-Diels-Alder reaction - cyclizations
-
1a
Acetylene Chemistry
Diederich F.Stang PJ.Tykwinski RR. Wiley-VCH; Weinheim: 2005. -
1b
Brandsma L. Synthesis of Acetylenes, Allenes and Cumulenes Elsevier; Amsterdam: 2004. - 2
Miller SI.Dickstein JI. Acc. Chem. Res. 1976, 9: 358 -
3a
Glaser C. Chem. Ber. 1869, 2: 422 -
3b
Hay A. J. Org. Chem. 1960, 25: 2928 -
3c
Hay A. J. Org. Chem. 1962, 27: 3320 -
3d
Tang J.-Y.Jiang H.-F.Deng G.-H.Zhou L. Youji Huaxue 2005, 25: 1503 -
3e
Bunz UHF. Chem. Rev. 2000, 100: 1605 - 4
Nakamura M. Pure Appl. Chem. 2006, 78: 425 - 5
Fürstner A.Davies PW. Chem. Commun. 2005, 2307 -
6a
Kimling H.Krebs A. Angew. Chem., Int. Ed. Engl. 1972, 11: 932 -
6b
Krebs A.Kimling H.Kemper R. Justus Liebigs Ann. Chem. 1978, 431 -
6c
Krebs A.Kemper R.Kimling H.Klaska K.-H.Klaska R. Liebigs Ann. Chem. 1979, 473 -
6d
Irngartinger H.Nixdorf M.Riegler NH.Krebs A.Kimling H.Maier G.Malsch K.-D.Schneider KA.Pocklington J. Chem. Ber. 1988, 121: 673 -
6e
Eisch JJ.Galle JE.Hallenbeck LE. J. Org. Chem. 1982, 47: 1610 -
6f
Eisch JJ.Hallenbeck LE.Lucarelli MA. J. Org. Chem. 1991, 56: 4095 -
6g
Grotjahn DB.Vollhardt KPC. J. Am. Chem. Soc. 1986, 108: 2091 -
6h
Sekiguchi A.Matsuo T.Watanave H. Phosphorus Sulfur Silicon Relat. Elem. 2001, 168: 51 -
7a
Bergman RG. J. Am. Chem. Soc. 1972, 94: 660 -
7b
Bergman RG. Acc. Chem. Res. 1973, 6: 25 -
7c
Lockhart TP.Bergman RG. J. Am. Chem. Soc. 1981, 103: 4091 - 8
Dai W.-M. Curr. Med. Chem. 2003, 10: 2265 -
9a
Smith AL.Hwang C.-K.Pitsinos EN.Scarlato GR.Nicolaou KC. J. Am. Chem. Soc. 1992, 114: 3134 -
9b
Nicolaou KC.Hummel CW.Pitsinos EN.Nakada M.Smith AL.Shibayama K.Saimoto H. J. Am. Chem. Soc. 1992, 114: 10082 -
10a
Kerwin SM.Nadipuram A. Synlett 2004, 1404 -
10b
Klein M.König B. Tetrahedron 2004, 60: 1087 - 11
Michael A.Bucher JE. Chem. Ber. 1895, 28: 2511 - 12
Pfeiffer P.Möller W. Chem. Ber. 1907, 40: 3841 -
13a
Bucher JE. J. Am. Chem. Soc. 1910, 32: 212 -
13b
Haworth RD.Sheldrick G. J. Chem. Soc. 1935, 636 -
13c
Haworth RD.Kelly W. J. Chem. Soc. 1936, 745 -
13d
Baddar FG.El-Assal LS.Doss NA. J. Chem. Soc. 1959, 1027 -
13e
Brown D.Stevenson R. J. Org. Chem. 1965, 30: 1759 -
13f
Klemm LH.Gopinath KW.Lee DH.Kelley FW.Trod E.McGuire TM. Tetrahedron 1966, 22: 1797 - 14
Müller E.Sauerbier M.Streichfuß D.Thomas R.Winter W.Zountsas G. Justus Liebigs Ann. Chem. 1971, 750: 63 - 15
Müller E.Odenigbo G. Justus Liebigs Ann. Chem. 1975, 1435 - 16
Wagner F.Meier H. Tetrahedron 1974, 30: 773 -
17a
Wessig P.Wettstein P.Giese B.Neuburger M.Zehnder M. Helv. Chim. Acta 1994, 77: 829 -
17b
Steiner A.Wessig P.Polborn K. Helv. Chim. Acta 1996, 79: 1843 -
17c
Lindemann U.Wulff-Molder D.Wessig P. J. Photochem. Photobiol., A 1998, 119: 73 -
17d
Wessig P.Schwarz J. Helv. Chim. Acta 1998, 81: 1803 -
17e
Lindemann U.Wulff-Molder D.Wessig P. Tetrahedron: Asymmetry 1998, 9: 4459 -
17f
Wessig P. Tetrahedron Lett. 1999, 40: 5987 -
17g
Wessig P.Schwarz J.Lindemann U.Holthausen MC. Synthesis 2001, 1258 -
17h
Wessig P.Mühling O. Angew. Chem. Int. Ed. 2001, 40: 1064 -
17i
Wessig P.Mühling O. Helv. Chim. Acta 2003, 86: 865 -
17j
Wessig P.Glombitza C.Müller G.Teubner J. J. Org. Chem. 2004, 69: 7582 -
17k
Wessig P.Mühling O. Angew. Chem. Int. Ed. 2005, 45: 6778 -
17l
Wessig P.Teubner J. Synlett 2006, 1543 -
18a
Wessig P.Müller G.Kühn A.Herre R.Blumenthal H.Troelenberg S. Synthesis 2005, 1445 - For another example of the PDDA reaction, see:
-
18b
Witte B.Margaretha P. J. Inf. Rec. 2000, 25: 225 - 19
Wessig P.Müller G.Herre R.Kühn A. Helv. Chim. Acta 2006, 89: 2694 - Compounds 5a-d have already been prepared by other methods. For 5a, see:
-
20a
Cox RJ.Ritson DJ.Dane TA.Berge J.Charmant JP.Kantacha A. Chem. Commun. 2005, 1037 - For 5b, see:
-
20b
Bellina F.Carpita A.Ciucci D.Santis M.Rossi R. Tetrahedron 1993, 49: 4677 - For 5c, see:
-
20c
Katrizky AR.Lang H. J. Org. Chem. 1995, 60: 7612 - For 5d, see:
-
20d
Van den Hoven BG.Ali BE.Alper H. J. Org. Chem. 2000, 65: 4131 -
21a
Dess DB.Martin JC. J. Org. Chem. 1983, 48: 4156 -
21b
Dess DB.Martin JC. J. Am. Chem. Soc. 1991, 113: 7277 -
22a
Bringmann G.Price Mortimer AJ.Keller PK.Gresser MJ.Garner J.Breuning M. Angew. Chem. Int. Ed. 2005, 44: 5384 -
22b
Cepanec I. Synthesis of Biaryls Elsevier; Amsterdam: 2004. -
23a
Berens U.Brown JM.Long J.Selke R. Tetrahedron: Asymmetry 1996, 7: 285 -
23b
Benincori T.Brenna E.Sannicolo F.Trimarco L.Antognazza P.Cesarotti E. J. Chem. Soc., Chem. Commun. 1995, 685 -
23c
Benincori T.Brenna E.Sannicolo F.Trimarco L.Antognazza P.Cesarotti E.Demartin F.Pilati T. J. Org. Chem. 1996, 61: 6244 -
24a
Fuji K.Node M.Tanaka F.Hosoi S. Tetrahedron Lett. 1989, 30: 2825 -
24b
Fuji K.Node M.Tanaka F. Tetrahedron Lett. 1990, 31: 6553 -
24c
Fuji K.Tanaka F.Node M. Tetrahedron Lett. 1991, 32: 7281 -
24d
Tanaka F.Node M.Tanaka K.Mizuchi M.Hosoi S.Nakayama M.Taga T.Fuji K. J. Am. Chem. Soc. 1995, 117: 12159 -
24e
Tanaka K.Ahn M.Watanabe Y.Fuji K. Tetrahedron: Asymmetry 1996, 7: 1771 -
24f
Ahn M.Tanaka K.Fuji K. J. Chem. Soc., Perkin Trans. 1 1998, 185 -
24g
Tada M.Nishiiri S.Zhixiang Y.Imai Y.Tajima S.Okazaki N.Kitano Y.Chiba K. J. Chem. Soc., Perkin Trans. 1 2000, 2657 - 25
Larock RC.Tu C.Pace P. J. Org. Chem. 1998, 63: 6859 -
26a
Bonifacio VDB. Synlett 2004, 1649 -
26b
Chen BC. Heterocycles 1991, 323: 529 -
27a
Toth G.Koever KE. Synth. Commun. 1995, 25: 3067 -
27b
Kawasaki N.Goto M.Kawabata S.Kometani T. Tetrahedron: Asymmetry 2001, 12: 585 -
27c
Englert HC.Gerlach U.Goegelein H.Hartung J.Heitsch H.Mania D.Scheidler S. J. Med. Chem. 2001, 44: 1085 - 28
Sonogashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 4467 - Compound 19a is commercially available. For the preparation of compound 19b, see:
-
29a
Ipaktschi J.Hosseinzahed R.Schlaf P.Eckert T. Helv. Chim. Acta 2000, 83: 1224 - For the preparation of compound 19c, see:
-
29b
Rao PNP.Uddin J.Knaus EE. J. Med. Chem. 2004, 47: 3972 - Compounds 22a-c have already been prepared by other methods. For 22a, see:
-
30a
Freeman F.Kim DSHL.Rodriguez E. J. Org. Chem. 1992, 57: 1722 - For 22b,c, see:
-
30b
Foud FS.Wright JM.Plourde G.Purohit AD.Wyatt JK.El-Shafy A.Hyad G.Crasto CF.Lin Y.Jones GB. J. Org. Chem. 2005, 70: 9789. For 22d,e, see ref. 18a - Compounds 32 have already been described in the literature. For 32, Ar2 = Ph, n = 1, see:
-
32a
Molinaro C.Jamison TF. J. Am. Chem. Soc. 2003, 125: 8076 - For 32, Ar2 = PMP, n = 1, see:
-
32b
Campi E. M., Chong J. M., Jackson W. R., van der Schoot M.; Tetrahedron; 1994, 50: 2533. For 32, Ar2 = 4-ClC6H4 and Ar2 = 4-F3CC6H4, n = 1, see ref. 18a. For 32, Ar2 = 1-naphthyl, n = 1, see:
-
32c
Feuerstein M.Berthiol F.Doucet H.Santelli M. Synthesis 2004, 1281 - For 32, Ar2 = Ph, n = 2, see:
-
32d
Roesch KR.Larock RC. J. Org. Chem. 2001, 66: 412 ; For Ar2 = 1-naphthyl, n = 2, see ref. 34 - 34
Wessig P.Müller G. Chem. Commun. 2006, 4524 - 35
March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1992. p.280 - 36
Klemm LH.Hsu Lee D.Gopinath KW.Klopfenstein CE. J. Org. Chem. 1966, 31: 2376 - 37
Yamaji M.Kobayashi J.Tobita S. Photochem. Photobiol. 2005, 4: 294 - 39 Compound 68 has already been described in the literature, see:
Choualeb A.Braunstein P.Rose J.Welter R. Inorg. Chem. 2004, 43: 57 - 40 The 1H NMR data of 29a, 69a and 70a have already been published, see:
Klemm LH.McGuire TM.Gopinath KW. J. Org. Chem. 1976, 41: 2571. The 13C NMR and MS data are given in Table 5
References
Compounds 33 were used without further purification.
33Analytical data of 23a and 24j are given in Table [5] . For 23b and 24k, see ref. 34. For 24a-i, see ref. 18a.
38Compounds 66 and 67 are commercially available.