Rhodium- or Copper-Catalysed CH-Insertion of Carbenoids into Dihydro­aromatic Compounds and Acyclic 1,4-Dienes

Abstract

A straightforward reaction sequence consisting of a cobalt-catalysed Diels-Alder reaction for the generation of dihydro­aromatic compounds and a rhodium- or alternatively a copper-catalysed CH-insertion reaction of carbenoids from diazo esters generates highly substituted benzene derivatives. When acyclic 1,4-dienes are synthesised by a cobalt-catalysed 1,4-hydrovinylation reaction, the rhodium-catalysed conversion with diazo esters leads to cyclopropanation rather than CH-insertion products.

catalysis - cobalt - copper - cyclopropanation - 1,4-diene

References

For reviews see:

1a Campeau LC. Fagnou K. Chem. Commun.  2006,  1253 

1b Metal-catalyzed Cross-coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998. 

1c Tsuji J. Palladium Reagents Catalysts   Wiley-VCH; Weimheim: 1995. 

1d Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 

1e Sonogashira K. In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pattenden G. Pergamon Press; New York: 1991.  p.521 

1f Negishi E. Anastasia L. Chem. Rev.  2003,  103:  1979 

For reviews see:

2a Davies HML. Loe O. Synthesis  2004,  2595 

2b Merlic CA. Zechman AL. Synthesis  2003,  1137 

2c Davies HML. Beckwith REJ. Chem. Rev.  2003,  103:  2861 

2d Lydon KM. McKervey MA. In Comprehensive Asymmetric Catalysis   Jacobsen EN. Pfaltz A. Yamamoto H. Springer; New York: 1999.  Chap. 16.2. p.539 

2e Dorwald FZ. Metal Carbenes in Organic Synthesis   Wiley-VCH; Weinheim: 1999. 

2f Arndtsen BA. Bergman RG. Mobley TA. Peterson TH. Acc. Chem. Res.  1995,  28:  154 

For selected recent examples see:

2g Davies HML. Jin Q. J. Am. Chem. Soc.  2004,  126:  10862 

2h Davies HML. Dal X. Long MS. J. Am. Chem. Soc.  2006,  128:  2485 

2i Davies HML. Manning JR. J. Am. Chem. Soc.  2006,  128:  1060 

2j Davies HML. Jin QH. Org. Lett.  2005,  7:  2293 

3a Davies HML. Gregg TM. Tetrahedron Lett.  2002,  43:  4951 

3b Davies HML. Walji AM. Townsend RJ. Tetrahedron Lett.  2002,  43:  4981 

3c Davies HML. Dai X. Long MS. J. Am. Chem. Soc.  2006,  128:  2485 

3d Davies HML. Manning JR. J. Am. Chem. Soc.  2006,  128:  1060 

3e Müller P. Tohill S. Tetrahedron  2000,  56:  1725 

For leading references, see:

4a Hilt G. Lüers S. Smolko KI. Org. Lett.  2005,  7:  251 

4b Hilt G. Lüers S. Harms K. J. Org. Chem.  2004,  69:  624 

4c Hilt G. Smolko KI. Angew. Chem. Int. Ed.  2003,  42:  2795 ; Angew. Chem. 2003, 115, 2901

5

Hilt, G.; Galbiati, F. Org. Lett. 2006, 8, 2195

6a Kirmse W. Angew. Chem. Int. Ed.  2003,  42:  1088 ; Angew. Chem. 2003, 115, 1120

6b Doyle MP. Forbes DC. Chem. Rev.  1998,  98:  911 

6c Pfaltz A. In Comprehensive Asymmetric Catalysis   Jacobsen EN. Pfaltz A. Yamamoto H. Springer; New York: 1999.  Chap. 16.1. p.513 

7 Nozaki H. Moriuti S. Takaya H. Noyori R. Tetrahedron Lett.  1966,  7:  5239 

8 Hilt G. Galbiati F. Synlett  2005,  828 

9 Hilt G. Smolko KI. Lotsch BV. Synlett  2002,  1081 

For reviews, see:

10a Valahovic MT. Keane JM. Harman WD. In Modern Arene Chemistry   Astruc D. Wiley; New York: 2002.  p.297 

10b Pape AR. Kaliappan KP. Kündig EP. Chem. Rev.  2000,  100:  2917 

11a Hilt G. du Mesnil F.-X. Lüers S. Angew. Chem. Int. Ed.  2001,  40:  387 ; Angew. Chem. 2001, 113, 408

11b Hilt G. Lüers S. Synthesis  2002,  609