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Zhang, H.; Liu, C.; Lei, A., Science of Synthesis: Catalytic Transformations via C—H Activation, (2015) 2, 167.
Various hetarenes 51 are converted into the corresponding heterocyclic carboxylic esters 52 in moderate to good yields through palladium-catalyzed aerobic oxidative C—H carbonylation (Scheme 27).[38] Substituted N-alkylindoles, thiophenes, and benzothiophenes 51 are suitable substrates under the standard reaction conditions. This transformation shows remarkably high regioselectivity.
Meeeee 88 Meeeeeeee-Meeeeeeee M—M Meeeeeeeeeeee ee Meeeeeeee[88]
Me8 | M8 | Meeeee (%) | Mee |
---|---|---|---|
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88e | [88] | |
(MM8)8Me | 88 | [88] | |
(MM8)88Me | 88 | [88] | |
(MM8)8eMe | 88 | [88] | |
MM(Me)(MM8)8Me | 88 | [88] | |
MM(Me)(MM8)8Me | 88 | [88] | |
MM(Me)(MM8)8Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88 | [88] | |
Me | 88e | [88] | |
Me | 88 (88)e,e | [88] | |
Me | 88e | [88] | |
MM(Me)(MM8)8Me | 88e | [88] |
e Meeeeeee eeeeee.
e 88 e.
e 88 °M.
e Mee eeeeeee eeee eeeeee; eeeeeeee eeeee ee M8 eeeeeeeeeeee eeeeeee ee eeeeeeeeeee.
e Meeeeeeeee: MeMe8(MMe8)8 (8 eee%), Me8M (88 eee%), Me(MMe)8 (8 eeeee), 888 °M, 88 e.
Meeeeee eeeeeeeeeee eeeeeee 88 (M8 ≠ M) ee eeee ee eeeeeee 88 (M8 = M) eeee eeee MM eee eeeeeeeeeeee eeee eeeeee eee eeeeee eeeeeeee ee eeee eee eeeeeee eeeeee-8-eeeeeeeeeeee 88 ee eee eeeeeeee ee e eeeeeee eeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeee-Meeeeeeee M—M Meeeeeeeeeeee ee Meeeeeeee[88]
M8 | M8 | M8 | M8 | M8 | Meeeee (%) | Mee |
---|---|---|---|---|---|---|
M | M | M | Me | Me | 88 | [88] |
M | M | M | Me | Me | 88 | [88] |
M | M | M | Me | (MM8)8Me | 88 | [88] |
M | M | M | Me | MMMeMe | 88 | [88] |
Me | M | M | Me | Me | 88 | [88] |
Me | M | M | Me | Me | 88 | [88] |
M | Me | M | Me | Me | 88 | [88] |
Me | M | M | Me | Me | 88 | [88] |
M | M | M | Me | Me | 88 | [88] |
M | M | M | Me | (MM8)8Me | 88 | [88] |
M | M | M | Me | eMe | 88 | [88] |
Me | M | M | Me | Me | 88 | [88] |
M | Me | M | Me | Me | 88 | [88] |
M | M | M | MM8MM=MM8 | Me | 88 | [88] |
Me | M | M | MM8MM=MM8 | Me | 88 | [88] |
M | Me | M | MM8MM=MM8 | Me | 88 | [88] |
Me | M | M | MM8MM=MM8 | Me | 88 | [88] |
M | M | M | Me | Me | 88 | [88] |
M | M | M | Me | Me | <8 | [88] |
Mee | M | M | Mee | Me | <8 | [88] |
M | M | M | Me | eeeeeee | 88 | [88] |
M | M | M | M | Me | 88e | [88] |
M | M | Me | M | Me | 88e | [88] |
M | Me | M | M | Me | 88e | [88] |
e Meeeeeee eeeeee.
e 88 °M, 88 e.
Meeeeeeeeeee Meeeeeeee
Meeee Meeeeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.
MeMe8(MMe8)8 (8.8 ee, 8.8 eee%), Me8M (8.8 ee, 8 eee%), eee e eeeeeeee 88 (8.8 eeee) eeee eeeeeeee ee ee eeee-eeeee Meeeeee eeee eeeeeeee eeee e eeeeeee eee. Me(MMe)8 (8.8 ee, 88 eee%) eee eeeee ee eee eeee ee e eeeeeeee. M eeeeeee eeeeee eeee MM eee eee (8:8) eee eeeeeeeee ee eee Meeeeee eeee eee eee eeee eeee eee eee eeee eee eeeeee eeeee eeeee. Me eeeeeee (M8MM; 8.8 eM), MMMM (8.8 eM), eee eeeeeee (8.8 eM) eeee eeeee ee eee eeee eee eeeeeee. Mee Meeeeee eeee eee eeeeee ee 888 °M eee 88 e eee eeee eeeeee ee ee. Mee eee eeeeeee eee eeeeeeeee eeeeeeee, eee eeeeeeee eee eeeeeeee eeee M8M, eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 ×). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe/Me8M).
Meeee Meeeee-8-eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.
Me eeeeee 88 (8.8 eeee), {MeMe(eee)}8 (8.88 eeee), M8M8M8 (8.8 eeee), ee eeeeeee (M8MM; 8.8 eeee), eee eeeeeee (8.8 eM) eeee eeeee ee e 88-eM Meeeeee eeee. Mee eeeee eeee eee eeeeeeeee eee eeeeee eeee MM (88.88% eeeeee) eeeee eeeee eeeeee ee eee eeeeeee eeeeeeeeeee eeee MM eee (8.8 eee). Mee eeee eee eeeeeee eeeee-eeeeee eee eeeeeeee ee ee eee eeee eeeeeeeee ee 888 °M. Mee eeeeeee eee eeeeeee eee 88 e eee eeee eeeeee ee ee. Meeeee MM eee eeeeeeeeee eee eee eeeeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee 888–888 eeee, eeeeeeeee eeeee/MeMMe 88:8 ee 8:8).
References
[38] | Meeee, M.; Mee, M.; Meee, M.; Mee, M.; Mee, M., Meee.–Mee. M., (8888) 88, 8888. |
[39] | Meee, M.; Me, M.; Mee, M.; Mee, M.; Me, M., Meee. Meeeee. (Meeeeeeee), (8888) 88, 88888. |