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
References
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
31 Compounds 33 were used without further purification.
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-ClC6 H4 and Ar2 = 4-F3 CC6 H4 , 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
33 Analytical data of 23a and 24j are given in Table
[5 ]
. For 23b and 24k , see ref. 34. For 24a -i , see ref. 18a.
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
38 Compounds 66 and 67 are commercially available.
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 1 H 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 13 C NMR and MS data are given in Table 5