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Ligandless Iron‐Catalyzed Desulfinylative C–C Allylation Reactions using Grignard Reagents and Alk‐2‐enesulfonyl Chlorides (Eur. J. Org. Chem. 36/2009)
Author(s) -
Volla Chandra M. R.,
Marković Dean,
Dubbaka Srinivas Reddy,
Vogel Pierre
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200990102
Subject(s) - chemistry , reagent , allylic rearrangement , sulfur dioxide , catalysis , sulfur , organic chemistry , grignard reaction , medicinal chemistry
The cover picture shows the iron door of the vineyard of Prof. Pierre Vogel in the Lavaux region, 12 km east of Lausanne along the Geneva Lake (Lac Léman) in Western Switzerland. This region is now part of the world heritage (UNESCO). The opened door symbolizes iron‐catalyzed reactions and, in particular, a new allylation reaction of inexpensive Grignard reagents with alk‐2‐enesulfonyl chlorides obtained in a new way that is the endergonic H‐ene reaction of sulfur dioxide with simple alkenes. The lake and the mountains in the background have been here for very long and will stay as such for much longer if civilization will concentrate on more sustainable development. Vineyards have existed in this area for more than 1200 years, and the grapes produced sometimes need a little sulfur dioxide to become a good wine (a practice that is ca. 8000 years old). The chemistry disclosed here uses sulfur dioxide for allylic C–H activation. The unstable alk‐2‐enesulfinic acids so obtained are oxidized with NCS to alk‐2‐enesulfonyl chlorides. The latter are then coupled with Grignard reagents under desulfinylation conditions and iron catalysis. Sulfur dioxide can be recovered. Details are discussed in the article by P. Vogel et al. on p. 6281 ff.