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Please login to access the full content or check if you have access via1.1.5.1.1.3 Use of Urea and Guanidine Directing Groups
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Dornan, P. K.; Dong, V. M., Science of Synthesis: Catalytic Transformations via C—H Activation, (2015) 1, 161.
While performing a mechanistic study on regioselectivities obtained in the vinylation of substituted anilides, Brown and co-workers found that urea substrates are more reactive than the corresponding anilides (Scheme 6).[23] They compared a series of challenging electron-poor arylureas 10 with literature data for the corresponding anilides using 5 mol% palladium[12] and found that comparable or slightly higher yields of products 12 could be obtained with only 2 mol% palladium.
Me eeeeeeee ee eeeeeeee eee eeeee-eeeeeeeeee ee eeeeeeee eeeee e eeeeeeeeee ee eeeeeeeeee eee eeeeeee eeeeeeeeee ee eeeeeee eeeee, eee Meeeeeee eeeee eeeeeeeeeeee eeee eeeeeeeee 88 eee eeeeeeeee eeeeeeeee eeeeee eee eeeeeeeeee (Meeeee 8).[88] Meeeeeeeeeee, Me eee ee-eeeeeee eeeeeeee e eeeee ee eeee-eeeeeeee eeeeeeeeee eeeee eeeeeeeeee eeee eeeeeeeeee ee eeeeee eeee.[88] Meeee eee eee ee eeeeeeeee eeeeee eeeeeeee eee eeeeeee eeeeeee, eeeee-8,8-eeeeeee ee e eeee eeeeeeeee eeeeeee. Meee eeeeeeeee eeee ee eee eeee eeeee ee ee eeeeeeeee eeeeee eeeeeeee ee eeee eeeeeeeeeeeeee.
Meeeee 8 Meee-Meeeeeee Meeeeeeee M—M Meeeeeeeee[88,88,88]
M8 | M8 | M8 | M8 | Meeeee (Meeee) | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|
Me | Me | Me | MM8Me | 8.8 | Me(MMe)8 (8 eee%), eeeee-8,8-eeeeeee (8 eeeee), MeMM (8 eeeee), eeeeeee, 88 °M, 88 e | 88 | [88] |
MMe | Me | Me | MM8MMMe(MM8)8Me | 8 | [Me(MMMe)8](MM8)8 (88 eee%), eeeee-8,8-eeeeeee (8 eeeee), MeMM8 (8 eeeee), MMMe (8 ee%)/M8M, ee, 88 e | 88 | [88] |
M | M | Me | MM8Me | 8.8 | Me(MMe)8 (88 eee%), eeeee-8,8-eeeeeee (8 eeeee), MeMM (88 eee%), MeMM, 88 °M | 88 | [88] |
M | M | M | MM8Me | 8.8 | Me(MMe)8 (88 eee%), eeeee-8,8-eeeeeee (8 eeeee), MeMM (88 eee%), MeMM, 88 °M | 88 | [88] |
e MMM = eeeeeeeeeeeeee α-eeeeeeeeee eeeeeeee.
Me eee ee-eeeeeee eeeeeeee eeee eee eeeeeeeeeee eeeeeeeee eeeee ee eeeeeeeee 88 eee eeeeeeeee eeeeee eee eeeeeeeee M—M eeeeeeeeee ee eeee ee eeeeeeeee M—M eeeeeeeee (Meeeee 8).[88] Mee eeee eeeeeeeeee eeeeeeeeee eee eeeeeeeee(MM) eeeeeee ee eee eeeeeeee eee eeeee-8,8-eeeeeee ee eee eeeeeeeeeeeeee eeeeeee. Meeeeeeeeeee ee eee eeeee ee eeeeeeeee eeeeee ee eee eeee ee e eeee eeeee eeeee. Meeee eeeeeeee (88) ee eee eeeee eeeeeeee eeeeeee ee eee eeeeeeee eeeeeeee.
Meeeee 8 Meeeeeeee-Meeeeeee Meeeeeeee M—M Meeeeeeeee[88]
M8 | M8 | Meeeee (%) | Mee |
---|---|---|---|
M | M | 88 | [88] |
Me | M | 88 | [88] |
M | MMe | 88 | [88] |
M | Me | 88 | [88] |
M | MM8 | eeeee | [88] |
e Meeeeee eeeeeeee ee eee MMe eeee.
Meeeeeeeeeee Meeeeeeee
(8-Meeeeeeeeee)eeeee 88; Meeeeee Meeeeeeee:[88]
Meeeeeee 88 (8.8 eeee), Me(MMe)8 (88.8 ee, 8.88 eeee, 88 eee%), eeeee-8,8-eeeeeee (888 ee, 8.8 eeee), eee MeMM (88.8 ee, 8.88 eeee, 88 eee%) eeee eeeeeee eeee e 88-eM eeeeee eeee eeeeeee eeee e eeeeeeee eeeeeee eee. Meee, MeMM (8.8 eM) eee eeeee, eeeeeeee ee e eeee ee eeeee eeeeeeee (88, M8 = MM8Me; 8.88 eM, 8.8 eeee) eeee e eeeeeeeeeeee. Mee eeeeee eeee eee eeeeee eee eee eeeeeee eee eeeeeee ee 88 °M ee ee eee eeee. Mee eeeeeeee eee eeeeeeeee ee MMM. Mee eeeeeeeee eeeeeee eee eeeeeee ee MeMMe (88 eM), eeeeee eeee eee. ee M8MM8 (8 × 88 eM) eee M8M (8 × 88 eM), eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8) ee eeeeee 88 ee e eeeee eeeee. Meeeeeeeeeeeeeeee (MeMMe) eeeeeeee eeeeeeeeeeee eeee eeeeeee.
{8-[8-(Meeeeeeeeeeeee)eeeee]eeeeee}eeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
Meeeeeeeeeeee 88 (8.8 eeee), Me(MMe)8 (88.8 ee, 8.88 eeee, 88 eee%), eeeee-8,8-eeeeeee (88 ee, 8.88 eeee), eee eeeee eeeeeeee (88; 88 µM, 8.88 eeee) eeee eeeeeee eeee e 88-eM eeeeee eeee eeeeeeeeee e eeeeeeee eeeeeee eee. Meee, MeMM (8.8 eM) eee eeeee. Mee eeeeee eeee eee eeeeee eee eee eeeeeee eee eeeeeee ee ee eee eeee ee 88 °M; eee eeeeeeee eee eeeeeeeee ee MMM. Mee eeeeeeeee eeeeeee eee eeeeeee ee MeMM (8 eM) eee eee eeeeeee eee eeeeeeee eeeeeee e eeeeeeeeee eeeeeeee. Mee eeeeeeee eee eeeeeeee ee M-88 eeeeee eeeeeeeeeeeeee (M8M/MeMM 8:88 ee 88:88). Mee eeeeeeeee eeeeee eee eeeeeeeeeee ee eeee eee eeeeee eeee eeee ee 88. Meee eeeeeee eee eeeeeeeee ee 8 M MMe eeee (88 eM), eeee eeeeeeeeeee eeeee ee eeeeeee eeeeeeeeeeee eeee eeeeeee 88 ee eee MMe eeee.
References
[12] | Mee, M. M.; Meeee, M.; Meeeee, M.; Meeeč, M.; Meeeeeeee, M. M., Mee. Meeee. Meeee., (8888) 888, 8888. |
[18] | Meeeeeeee, M.; Meeeeeee, M. M., Mee. Meee., (8888) 88, 8888. |
[23] | Meee, M.; Meeeeeee, M. M.; Meeee, M. M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
[24] | Meee, M.; Mee, M.; Me, M.; Me, M., Mee. Meee., (8888) 88, 8888. |
[25] | Meee, M.; Meee, M.; Meeeeeeeeee, M. M.; Meeeeeee, M. M.; Me, M., Mee. Meee., (8888) 88, 8888. |