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Joule, J. A., Science of Synthesis Knowledge Updates, (2018) 2, 125.
Only a couple of examples exist in which an amino group displaces a halogen from a 4-(2-aminoaryl)-3-halopyridine, for instance, 2-(3-chloropyridin-4-yl)aniline 376 is transformed into the cyclized product 377 by palladium catalysis with 2-(dicyclohexylphosphino)biphenyl (102) as ligand (Scheme 138),[164] but there are many more examples in which the nitrogen of an acetamide or sulfonamide serves this purpose (see Sections 10.23.2.1.1.4.3.5 and 10.23.2.1.1.4.3.6).
Meeeee 888 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeee Meeeeeeee eeee ee 8-(8-Meeeeeeeeee-8-ee)eeeeeee[888]
Me eee eeeeeee eeee ee 8-(8-eeeeeeeeeeeee-8-ee)eeeeeee 888, eeee e eeeeeee eeeeeeeee ee eee eeeee eeeeee eeeee, eee eeeeeee eee ee eeeeeeeee ee eee eeeee eeeee eeeeee ee eeeeeee eeee eeeeeeeeee eeeeeeee ee eeee 888 °M eeeeee 8M-eeeeee[8,8-e]eeeeee 888 ee 88% eeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeeeeee Meeeeeeee eeee e 8-(8-Meeeeeeeeeeee-8-ee)eeeeeee[888]
Meeeeeeeeeee Meeeeeeee
(M)-8-Meeeee-8-(8-eeeeeeeeeeeeeeee-8-ee)-8M-eeeeee[8,8-e]eeeeee (888); Meeeeee Meeeeeeee:[888]
M eeee ee 8-{8-eeeeee-8-eeeeee-8-[(M)-8-eeeeeeeeeeeeeeee-8-ee]eeeeeee-8-ee}eeeeeee (888; 88 ee, 8.888 eeee, 8.8 eeeee), Me8(eee)8 (8 ee, 8 µeee, 8.8 eeeee), 8-(eeeeeeeeeeeeeeeeeeeee)eeeeeeee (888; 8 ee, 8.888 eeee, 8.8 eeeee), eee Me8MM8 (88 ee, 8.88 eeee, 8.8 eeeee) ee 8,8-eeeeeee (8 eM) eee eeeeeeee eeee eeeee eee 88 eee eee eeee eeeeee ee 888 °M eee 88 e. Mee eeeeeee eee eeeeee ee ee, eeeeee eeee eee. ee MeMMM8, eee eeeeeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (M8MM8), eeeeeeee eeeeeee Meeeee, eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee MMM (eeeeee eee, MeMM/MM8Me8 8:88) ee eeeeee eee eeeeeee ee ee eee-eeeee eeeee; eeeee: 88 ee (88%); ee 888–888 °M.
8-Meeeee-8-(8M-eeeeee[8,8-e]eeeee-8-ee)eeeee-8-eee (888); Meeeeee Meeeeeeee:[888]
Meeee eee (888 °M) ee•MMe (88 e) eee eeeee ee 8-[8-(8-eeeeeeeeeee)-8-eeeeeeeeeeeee-8-ee]-8-eeeeeeeeeee-8-eee (888; 88 ee, 8.88 eeee) eee eee eeeeeee eee eeeeee ee 888 °M eee 88 eee. Mee eeeeeeeee eee eeee eee eeeeee eeee e eeeeeee ee eee eee eeeee MM8. Mee eeeeeee eeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee, eeeeeeeee eee eeeeee eeeeeee; eeeee: 88%; ee 888 °M.
References
[164] | Meeeee, M. M.; Meeeee, M. M., Mee. Meee., (8888) 8, 8888. |
[165] | Meeee, M.; Meeeeee, M.; Meeeee, M.; Meéeeeeee, M.; Meeee, M.; Mee, M., Meeee. Meeeee., (8888) 88, 8888. |