You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via8.1.14.2.2 Variation 2: Amide Directed ortho-Lithiation Groups
Please login to access the full content or check if you have access via
Gribble, G. W., Science of Synthesis, (2006) 8, 364.
The seminal work by Beak,[19,57,69–72] Snieckus,[8,11,13,19,73] and Gschwend[16,74,75] demonstrates the importance of the amide directing group in aromatic lithiation. Examples 19, 21, and 22 in Scheme 9 are representative. Further reaction of aryllithium compound 19 with an electrophile, e.g. benzaldehyde, gives substituted benzamides such as 20.[73]
Meeeee 8 Meeeeeee Meeee-Meeeeeee eeeee-Meeeeeeeee Meeeeeeee[88,88,88]
Meeeeee eeeeeeeeeeee eeeeeeeee eeee eee ee eee eeeeeeeee eee eeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeeee ee Meeeee 88.[88–88]
Meeeee 88 Meeeeeee Meeeeeeee Meeeee[88–88]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeee Meeeeeeeee, e.e. 88; Meeeeee Meeeeeeee:[88]
Me e eeeeeee eeee ee e M,M-eeeeeeeeeeeeeeee (8.8 eeee) ee MMM (88 eM) eeeee M8 ee −88°M (eee eee/eeeeeee eeee) eee eeeeeeee eeeeeeeeeeee eeeeeee e eeeeee eeeee MMMMM (8.8 eeee) eee e-MeMe (8.8 eeee). Mee eeee eee eeeeeee ee −88°M eee 8 e. Me eeee eeee, eee eeeeeeeeeeee (8.8 eeee) eee eeeee eee eee eeee eee eeeeeee ee eeee ee ee eeee 8–88 e, ee eeeee eeee eee eeeeeee eee eeeeeee eeee eee. ee MM8Me eeee eeeeeeee ee eeeeeeeeee eeee MM8Me8. Mee eeeeeee eeeeeee eee eeeee (Me8MM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeee eeeeeee. Meeeeeeeee eeeee eeeeeeeeeeeeee ee eee eeeee eeeeeeee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeee eee eeee eeeeeee; eeeee: 88–88%.
References
| [8] | Meeee, M.; Meeeeee, M.; Meeeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [11] | Meeeeeee, M., Meee. Mee., (8888) 88, 888. |
| [13] | Meeeeee, M.; Meeeeeee, M., Me Meeeee Meeee Meeeeeeee, Meeeee, M., Me.; Meeee: Mee Meee, (8888); e 888. |
| [16] | Meeeeeee, M. M.; Meeeeeeee, M. M., Mee. Meeee. (M. M.), (8888) 88, 8. |
| [19] | Meee, M.; Meeeeeee, M., Mee. Meee. Mee., (8888) 88, 888. |
| [57] | Meee, M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [69] | Meee, M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 88. |
| [70] | Meee, M.; Mee, M.; Meeeeee, M.; Meee, M.-M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [71] | Meee, M.; Meeeeee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [72] | Meeeeeee, M. M.; Meeeeee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [73] | ee Meeee, M. M.; Meee, M. M.; Meeeeeeee, M. M.; Meee, M.; Meeeee, M. M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [74] | Meeeee, M.; Meeeeeee, M. M.; MeMeeee, M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [75] | Meeeee, M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [76] | Meeeeeeee, M. M.; Mee, M.-M., Mee. Meee. Meeeee. Mee., (8888) 88, 888. |
| [77] | Meeeeeeeee, M.; Meeeeeeee, M.; Meeeeeee, M., Mee. Meee., (8888) 8, 8888. |
| [78] | Meeeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [79] | Meeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [80] | Meeeee, M.; Meee, M.; Meeee, M.; Mee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
Return to Top