You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via2.7.2.1.2 Chlorination with Other Chlorine-Containing Oxidants
Please login to access the full content or check if you have access via
Sanford, M. S.; Cook, A., Science of Synthesis: Catalytic Transformations via C—H Activation, (2015) 2, 192.
Other chlorine-containing oxidants have also been used to effect metal-catalyzed, ligand-directed Caryl—H chlorination. These include 4-toluenesulfonyl chloride,[16] tert-butyl hypochlorite,[17] benzoyl chloride,[18] and 2,3-dichloro-5,6-dicyanobenzo-1,4-quinone (DDQ).[19] The vast majority of reported reactions involve 2-arylpyridine substrates.
Meee 8-eeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeeee/eeeeeee, eee(eeeeeeeeeeee)eeeeeeeeeeeeeeeee(MM) eee eeeeee(MM) eeeeeeee eee eeee ee eeeeeeeeeee, eee eeee eeeeeeee-eeee 8-eeeeeeeeeeee eeeeeeeeee 88 eeee eeee eeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee-Meeeeeeee Meeee—M Meeeeeeeeeee ee 8-Meeeeeeeeeeee eeee 8-Meeeeeeeeeeeeee Meeeeeee[88]
| M8 | M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|---|
| M | Me | M | 88 | [88] |
| M | M | M | 88 | [88] |
| Me | M | M | 88 | [88] |
| M | M | MMe | 88 | [88] |
Meeeee(M) eeeeeeeeeeeeeeeeeeeeeeeee ee eeee ee eee eeeeeeee eee eee eeee-eeeee eeeeeeeeeeee eeeeeeee eeeeeeeeeeee ee eeeeeeee-eeee 8-eeeeeeeeeeee eeeeeeeeee (Meeeee 88).[88] Me eeee eeeeee, eeeeeeeeee eeeeee ee Meeee—M eeeeeeeeeeee eeeeeeee 88 eee eeeeeeee eeee eeeeeeeeee eeeeeee eeeeeeee-eeeeeeeeeee eeeeee (e.e., 88, M8 = MM8Me). Me eeeeeeeeee eeeeeeeeee eeeeeeee eeeeeeee-eeeeeeee eeeeeee eeeeee ee eee eeeeeeee eeee (e.e., 88), eeeeeeeeeeee eeeeee eeeee ee eee eeeeeee eeeeeeeeeeee, eeeeeeeeee eee e eeeeeeeeeee eee-eeeeeeee eeeeeeeeeeeee eeeeeeee eeeeeeeeeeee eeeeeee.
Meeeee 88 Meeeee-Meeeeeeee Meeee—M Meeeeeeeeeee ee 8-Meeeeeeeeeeee eeee eeee-Meeee Meeeeeeeeeee[88]
| M8 | Meeee (%) | Mee |
|---|---|---|
| M | 88 | [88] |
| Me | 88 | [88] |
| MM8Me | 8 | [88] |
Mee eeeeeeeee eeee eeeeeee eeeeeeee ee eee eeeeeeee eeeeee/eeeeeee eee eeeeeeeee ee eeeeee(MM) eeeeeee (Meeeee 88). Meee eeeeee ee eeeeeeeee eee eee eeeee-Meeee—M eeeeeeeeeeee ee 8-eeeeeeeeeeeee 88 eeeeeee eeeeeeee-eeeeeeee eeeeee eee eeeeeeee eeeeee eeeeeee eeee 88 ee 88%.[88]
Meeeee 88 Meeeee-Meeeeeeee Meeee—M Meeeeeeeeeee ee 8-Meeeeeeeeeeee eeee Meeeeee Meeeeeee[88]
| M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|
| M | M | 88 | [88] |
| M | MMe | 88 | [88] |
| M | Me | 88 | [88] |
| Me | M | 88 | [88] |
8,8-Meeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee eee eeee ee eeee ee eee eeeeeee eee eeeeeeee eeeeee eee eee eeeeeeeee(MM) eeeeeeee eeeeeeeee eeeee-eeeeeeeeeeee ee 8-eeeeeeeeeeeee (Meeeee 88).[88] Me eeeeeeeeee eeeeeee eee eeeeeeeeee eeeeeee Meeee—M eeee (e.e., 88), eeeeeeeeeeeeeeee ee eeeeeeee. Meeeeee, ee eeeee eeee eeee ee eee Meeee—M eeeee eeeee ee eee eeeeeeeee eeeee eee eeeeeee eeeeeeeeee, ee ee 8-eeeeeeeeeeeee 88, eeeeeeeeeeeeee eeeeeeee 88 eee eeeeeeee ee eee eeeee eeeeeeee.
Meeeee 88 Meeeeeeee-Meeeeeeee Meeee—M Meeeeeeeeeee ee 8-Meeeeeeeeeeee eeee 8,8-Meeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee[88]
| M8 | Meeee (%) | Mee |
|---|---|---|
| M | 88 | [88] |
| Me | 88 | [88] |
| MM8Me | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
8-(8-Meeeee-8-eeeeeeeeeeee)eeeeeeee (88, M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[88]
8-(8-Meeee)eeeeeeee (88, M8 = M8 = M; M8 = Me; 8.8 eeee, 8 eeeee), MeMe8(MMMe)8 (8.8 ee, 8.88 eeee, 8.8 eeeee), MeMe (888.8 ee, 8.8 eeee, 8 eeeee), eee MMM (8 eM) eeee eeeeeeee ee e 88-eM Meeeeee eeeee, eee eee eeeeeee eee eeeeeee ee 888 °M eee 88 e. Mee eeeeeee eee eeee eeeeee ee ee, eee ee Me8M (88 eM) eee eeeee. Meee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM), eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (8 × 88 eM) eee eeeee (Me8MM8). Mee eeeeeee eeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMMe 88:8); eeeee: 88%. Meee: Me eee eeeeeeee eeeee, MeMe8 (88 eee%) ee eeeee ee eee eeeeeeee eeeeee eee eeee ee eee eeeeeeeee ee eee eeeeeeeeeeee eeeeeeeee.
8-(8-Meeeeeeeeeee)eeeeeeee (88, M8 = M); Meeeeee Meeeeeeee:[88]
M eeeeeee ee 8-eeeeeeeeeeeeee (88, M8 = M; 88 ee, 8.8 eeee, 8 eeeee), e-MeMMe (888 ee, 8.88 eeee, 8.8 eeeee), MeMMe (88 ee, 8.88 eeee, 88 eee %), eee MeMM (8 eM) eee eeeeeeee eeeee M8 eee 8 e. Mee eeeeeee eee eeeeee ee ee eee eeeeeeee. Mee eeeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8); eeeee: 88%.
8-(8-Meeeee-8-eeeeeeeeeeeee)eeeeeeee (88, M8 = M; M8 = MMe); Meeeeee Meeeeeeee:[88]
8-(8-Meeeeeeeeeeee)eeeeeeee (88, M8 = M; M8 = MMe; 8.8 eeee, 8 eeeee), MeMe (8.8 eeee, 8 eeeee), Me(MMe)8 (8.8 ee, 8.88 eeee, 8.8 eeeee), Me8MM8 (88.8 ee, 8.8 eeee, 8 eeeee), eee eee eeeeeee (8 eM) eeee eeeeeeee ee e eeee, eeeee eee eeee eeeeee eeeee M8, eeeeee, eee eeeeee ee 888 °M eee 88 e. Mee eeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.
8-(8-Meeeee-8-eeeeeeeeeeeee)eeeeeeee (88); Meeeeee Meeeeeeee:[88]
8-(8-Meeeeeeeeeeee)eeeeeeee (88; 8.8 eeee, 8 eeeee), MMM (8.8 eeee, 8 eeeee), MeMe8 (8.88 eeeee), eee MMM (8 eM) eeee eeeeee ee 888 °M eee 8 e. Mee eeeeeee eee eeee eeeee ee M8M (88 eM) eee eeee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8); eeeee: 88%.
References
| [16] | Meee, M.; Meeeeeeeeeeć, M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [17] | Me, M.; Meeee, M.; Me, M., Meee. M. Meee., (8888) 88, 8888. |
| [18] | Meee, M.; Mee, M.; Meee, M.; Meeee, M., Meee. Meeeee. (Meeeeeeee), (8888) 88, 8888. |
| [19] | Meeee, M.; Meee, M.; Me, M., Mee. Meee. Meeee., (8888) 8, 888. |
Return to Top