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Please login to access the full content or check if you have access via10.13.1.1.1.3.1.9.4 Variation 4: Using Hydroamination
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Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 65.
A different mechanism is involved in the reaction between 2-bromo- or 2-chloroanilines and internal alkynes catalyzed by titanium(IV) chloride (Scheme 81): an enamine intermediate 227 is involved and the ring closure requires an intramolecular Heck reaction to give the indoles 228.[258]
Meeeee 88 Mee ee Meeeeeeeeeeeee[888]
| Me8 | M8 | Meeee (%) | Mee |
|---|---|---|---|
| Me | Me | 88 | [888] |
| Me | (MM8)8Me | 88 | [888] |
| 8-MeMM8M8 | (MM8)8Me | 88 | [888] |
| 8-M8MM8M8 | Me | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeee-8M-eeeeee (888, Me8 = M8 = Me); Meeeeee Meeeeeeee:[888]
8-Meeeeeeeeeeee (888 ee, 8.88 eeee) eee eeeeeeeeeeeeeeeee (8.88 e, 8.88 eeee) eeee eeeee ee e eeee ee MeMe8 (8.88 eM, 8.88 eeee) eee e-MeMM8 (8.88 eM, 8.88 eeee) ee eeeeeee (8 eM) eee eee eeeeeeeee eeeeeee eee eeeeeee eee 88 e ee 888°M. Mee eeeeeee eee eeeeeeeee eeeeeee eee e-MeMM (8.88 e, 88.8 eeee), 8,8-eee(8,8-eeeeeeeeeeeeeeeee)-8M-eeeeeeee-8-eee eeeeeeee (MMMeMe, 88; 888 ee, 8.88 eeee), eee Me(MMe)8 (888 ee, 8.88 eeee) eeee eeeee. Mee eeeeeee eee eeeeeee ee 888°M eee 88 e eee eeee MM8Me8 (88 eM) eee 8 M ee MMe (88 eM) eeee eeeee ee eee eeee eeeeeeeeee. Mee eeeeeeeee eeeeeee eeeee eee ee-eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eee. ee MeMMM8 (88 eM) eee eeeee (88 eM), eeeee (MeMM8), eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/Me8M) ee eeee eee eeeeeee ee ee eee-eeeee eeeee; eeeee: 888 ee (88%).
References
| [258] | Meeeeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
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