Synthesis of C1-Substituted Oxabenzonorbornadienes

Abstract

Oxabenzonorbornadienes are valuable synthetic intermediates because they can serve as a general template with which to create highly substituted ring systems. However, to date, only very few C1-substituted oxabenzonorbornadienes have been reported. In this study, the synthesis of some C1-substituted oxabenzonorbornadienes was achieved by the Diels–Alder reaction between 2-substituted furans and benzyne. Moderate to good yields (16–80%) of the Diels–Alder reactions were observed. These C1-substituted oxabenzonorbornadienes will find applications as valuable synthetic intermediates and should be useful in studies of transition-metal-catalyzed reactions.

Key words

cycloaddition - Diels–Alder reaction - benzyne - furan - alkenes

• References

• 1 Rayabarapu DK, Cheng C.-H. Acc. Chem. Res. 2007; 40: 971
• 2 Lautens M, Fagnou K, Heibert S. Acc. Chem. Res. 2003; 36: 48
• 3 Padwa A, Wang Q. J. Org. Chem. 2006; 71: 7391
• 4 Cho Y, Zunic V, Senboku H, Olsen M, Lautens M. J. Am. Chem. Soc. 2006; 128: 6837
• 5 Chen CL, Martin SF. J. Org. Chem. 2006; 71: 4810
• 6 Burton RR, Tam W. J. Org. Chem. 2007; 72: 7333
• 7 Burton RR, Tam W. Tetrahedron Lett. 2006; 47: 7185
• 8 Villeneuve K, Tam W. Eur. J. Org. Chem. 2006; 5499
• 9 Villeneuve K, Tam W. Organometallics 2007; 26: 6082
• 10 Villeneuve K, Tam W. Organometallics 2006; 25: 843
• 11 Villeneuve K, Tam W. J. Am. Chem. Soc. 2006; 128: 3514
• 12 Ballantine M, Menard ML, Tam W. J. Org. Chem. 2009; 74: 7570
• 13 Allen A, Le Marquand P, Burton R, Villeneuve K, Tam W. J. Org. Chem. 2007; 72: 7849
• 14 Mirsadeghi S, Rickborn B. J. Org. Chem. 1986; 51: 986
• 15 Best WM, Collins PA, McCulloch RM, Wege D. Aust. J. Chem. 1982; 35: 843
• 16 Villeneuve K, Tam W. Eur. J. Org. Chem. 2006; 5449
• 17 Raheem M.-A, Nagireddy JR, Durham R, Tam W. Synth. Commun. 2010; 40: 2138
• 18 Haner J, Jack K, Nagireddy JR, Raheem M.-A, Durham R, Tam W. Synthesis 2010; 721
• 19 Nolan SM, Cohen T. J. Org. Chem. 1981; 46: 2473