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Afarinkia, K.; Vinader, V., Science of Synthesis, (2003) 14, 309.
Displacement of a halogen group for an alkenyl or aryl group is a particularly attractive method for the preparation of 2H-pyran-2-ones for two reasons. Firstly, it allows a diverse range of analogues to be prepared from a single molecule, making parallel synthesis viable and efficient. Secondly, it allows access to a number of 2H-pyran-2-ones that would be difficult to make otherwise. For instance, 2H-pyran-2-ones bearing only a 5-alkenyl or 5-aryl substituent are difficult to make by cyclization routes, whereas they are easily made by coupling reactions. Both Suzuki (Scheme 65 and Table 7) and Stille (Scheme 66) couplings have been reported, as well as some palladium-catalyzed displacements.[6,222,228–231]
Meeeee 88 Meeeee Meeeeeee ee 8-Meeee-8M-eeeee-8-eee[888]
Meeee 8 Meeeee Meeeeeee ee 8-Meeee-8M-eeeee-8-eee[888]
M8 | Meeee (%) | Mee |
---|---|---|
Me | 88 | [888] |
8-MeMM8M8 | 88 | [888] |
8-MeMM8M8 | 88 | [888] |
8-MeMM8M8 | 88 | [888] |
8-MM8M8 | 88 | [888] |
Meeeee 88 Meeeee Meeeeeee ee 8-(Meeeeeeeeeeeeeee)-8M-eeeee-8-eee[8]
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8M-eeeee-8-eee (88); Meeeeee Meeeeeeee:[888]
M 88-eM, eee-eeeeee, eeeee-eeeeeeee eeeee eee eeeeeee eeee 8-eeeee-8M-eeeee-8-eee (8.888 e, 8.88 eeee), Me(MMe8)8 (88 ee, 8.88 eeee), eee eeeeeee (88 eM). Me eeee eeeeeeeeee eeeeeee eeeeeee eee eeeee eeeeeeeeeeeee eeee (8.888 e, 8.88 eeee) eeeeeeeee ee e eeeeeee eeeeee ee 88% MeMM (ee. 8 eM) eee 8 M ee Me8MM8 eeee (8.88 eM, 8.88 eeee). Meee eeeeeee eee eeeeee eee 8 e ee 88°M eeeee e M8 eeeeeeeeee. Mee eeeeeee eee eeeeeee eeee eee eeeeee eeeeeee eee eee eeeee eeeeeee eee eeeeeeeee eeee MM8Me8 (88 eM). Mee eeeeeeee eeee eeeeee eeee eee. ee MeMe eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee [eeeeee eee, MeMMe/eeeeeeeee eeeee (ee 88–88°M) 8:8]. Meeeeee ee eee eeeeeee eeee eeeeeeeeeee eeeeeeeee eeeeeeee eee eeeeeee eeeeeee ee e eeeeee eeeee; eeeee: 888 ee (88%); ee 88°M.
8-(Meeeeeeeee-8-ee)-8M-eeeee-8-eee (88); Meeeeee Meeeeeeee:[8]
M eeeeeee ee 8-(eeeeeeeeeeeeeeee)-8M-eeeee-8-eee (eee Meeeeee 88.8.8.8.8.8) (888 ee, 8 eeee), eeeeeeeeee-8-ee eeeeeeee (888 ee, 8.88 eeee), MeMe (888 ee, 88.88 eeee), eee Me(MMe8)8 (88 ee, 8.88 eeee) ee MMM (8 eM) eee eeeeeeee eeeee ee eeeee eeeeeeeeee eee 88 e. Mee eeeeee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee eeeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee 8.8:8.8) ee eeeeee e eeeeeeeee eee; eeeee: 888 ee (88%).
References
[6] | Mee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[222] | Meeeeee, M.; Meeeee-Meeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[228] | Meeeeeeee, M.; Meeee-Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[229] | Mee, M.; Meee, M. M.; Mee, M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 88. |
[230] | Meeeeee, M.; Meeee, M.; Meeeeeeeee, M.; Meeeeeeeee, M.; Meeeeee, M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 88888. |
[231] | Mee, M. M.; Meeeee, M. M., Meeeeee, (8888), 888. |