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Sandrock, D. L., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 1, 341.
The preparation of potassium (alkoxymethyl)trifluoroborates and their cross coupling with aryl and hetaryl halides can be performed to install alkoxymethyl groups on the arenes or hetarenes, giving (alkoxymethyl)arenes 25.[35] Using palladium(II) acetate and RuPhos, a variety of substrates have been utilized in this context (Scheme 18).
Meeeee 88 Meeee Meeeeeee ee (Meeeeeeeeeee)eeeeeeeeeeeeeeee eeee Meee eee Meeeeee Meeeeee[88]
M8 | Me8 | M | Meeee (%) | Mee |
---|---|---|---|---|
Me | 8,8-Me8M8M8 | Me | 88 | [88] |
Me | Me | 88 | [88] | |
e-Me | 8-MMM8M8 | Me | 88 | [88] |
(MM8)8MMM | 8-MMM8M8 | Me | 88 | [88] |
(MM8)8MMM | Me | 88 | [88] | |
(MM8)8MMM | 8-eeeeeee | Me | 88 | [88] |
Meeeeeeeeeee eeeeee eee eeee ee eeeeeeeee ee eeeeeeeee ee eee eeeee eeeeeeee ee (eeeeeeeeeeee)eeeeeeeeeeeeeeee eeee eeee eee eeeeeee eeeeeeeeeeeeeeeee. Meee M—M eeeeeeeeee eeeeeeee eee eeeeeeeeeeeee eeeee-eeeeeee (eeeeeeeeeeee)eeeeee 88 ee eeee eeeeee eee e eeeee ee eeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeee Meeeeeee ee (Meeeeeeeeeee)eeeeeeeeeeeeeeee eeee Meee eee Meeeeee Meeeeeeeeeeeeeeee[88]
M8 | Me8 | Me eeeeeeee (eee%) | 88 (eee%) | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | 8-eeeeeeee | MeMe8(eee) (8) | 88 | 88 | [88] |
e-Me | 8-eeeeeeee | MeMe8(eee) (8) | 88 | 88 | [88] |
(MM8)8MMM | 8-eeeeeeee | MeMe8(eee) (8) | 88 | 88 | [88] |
Me | 8-eeeeeeee | 88 (8) | 8 | 88 | [88] |
Me | 88 (8) | 88 | 88 | [88] | |
Me | 88 (8) | 8 | 88 | [88] |
Mee eeeee eeeeeeee ee eeeeeeeee (eeeeeeeeeeeee)eeeeeeeeeeeeeee eeee eeee eeeeeee eee eeeeeeeeeeeeeeeeeeeeeeeeee eee eeee eeee eeeeeeeee.[88] Meeee eeee eeeeeeee, e eeeeeeeeeeeee eeeee eee ee eeeeeeee eeeeeeeee eeee ee eeeeeeee ee eeeeeeeeeeeeee eeee eeeeee ee eeee eeeeeeee 88 eeeeeee e eeeeeeee eeeeeeeeeeee eeee ee eeeeee eee eeee eeeeeee. Meee eeeeeeeeeeeeee eee ee eeeeeeeeeeee ee eeee ee eeeeeeeee eeeeee eeeee 8 eee% ee eee(eeeeeeeeeeeeeeeeeeee)eeeeeeeee(8) eee 88 eee% ee MeMeee (Meeeee 88).
Meeeee 88 Meeee Meeeeeee ee Meeeeeeee (Meeeeeeeeeeee)eeeeeeeeeeeeeee eeee Meee Meeeeee eee Meeeeeeeeeeeeeeeeeeeeeeeee[88]
Me8 | M | Meeee (%) | Mee |
---|---|---|---|
8-eeeeeeee | Me | 88 | [88] |
8-M8MMMM8M8 | Me | 88 | [88] |
8-M8MM8M8 | Me | 88 | [88] |
MMe | 88 | [88] | |
8-eeeeeeee | Me | 88 | [88] |
Me | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
(Meeeeeeeeeee)eeeeee 88; Meeeeee Meeeeeeee:[88]
Meee e Meeeeee eeeeeeeee eeee eeee eeeee eee (eeeeeeeeeeee)eeeeeeeeeeeeeee (8.88 eeee), Me(MMe)8 (8.8 ee, 8.888 eeee), MeMeee (88 ee, 8.88 eeee), eee Me8MM8 (888 ee, 8.8 eeee, ee eeeeeeee). Mee eeee eee eeeeee eeee e MMMM-eeeee eeeeeeeeee eeeeee eee eee eeeeee eeee M8. Me eee eeeeeee eee eeeee eee eeeeeeeeeeee (8.8 eeee) eee eeeeeee/M8M (88:8; 8 eM), eee eee eeeeeee eee eeeeeee ee 888 °M. Meeee 88 e, eee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeeeee eeee MeMMe (8 ×). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee eee eeeee (MeMM8), eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
(Meeeeeeeeeee)eeeeee 88; Meeeeee Meeeeeeee:[88]
M Meeeeee eeee eee eeeeeee eeee MeMe8(eee) (8.8 ee, 8.8 µeee) ee (8′-eeeeeeeeeeeee-8-ee)eeeeeeeeeeeeeee(MM) eeeee (88; 8.8 ee, 88 µeee), eeeee (88; 8.8 ee, 88 µeee ee 88.8 ee, 88.8 µeee), eee (eeeeeeeeeeee)eeeeeeeeeeeeeee (8.88 eeee), eee eeeeeeeeeeeeeeee (8.88 eee), eee M8MM8 (888 ee, 8.88 eeee). Mee eeee eee eeeeee eeee e MMMM-eeeee eeeeee eee eeeeee eeee eeeee (8 ×). e-MeMM/M8M (8:8; 8.8 eM) eee eeeee eeeee eeeee, eee eee eeeeeee eee eeeeee ee 888 °M eee 88 e eee eeee eeeeeee ee eeee ee ee. Mee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM) eee eeee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeee eeeeeeeeeeeeee (eeeeee eee).
Meeeeeee Meeeeeee 88; Meeeeee Meeeeeeee:[88]
M Meeeeee eeee eee eeeeeee eeee eee eeeeeeeeeeee (8.888 eeee), Me(eee)8 (8.88 ee, 8.888 eeee), MeMeee (8.88 ee, 8.888 eeee), Me8MM8 (88.8 ee, 8.888 eeee), eeeeeeeee (eeeeeeeeeeeee)eeeeeeeeeeeeeee (88.8 ee, 8.888 eeee), 8.8-eeeeeee (8.8 eM), eee eeeeeeeee M8M (888 µM). Mee eeee eee eeeeee eeee e eeeeeeeeee eee, eee eee eeeeeee eee eeeeee ee eeeeee eeee eeeeeeee eee 88 e eeeee M8, eeeeeee ee eeee ee ee, eee eeee eeeeeeee eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeee eeeeeeeeeeeeee (eeeeee eee).
References
[35] | Meeeeeee, M. M.; Meeeeee, M., Mee. Meee., (8888) 88, 8888. |
[36] | Meeeeeee, M. M.; Meeeeeee, M., Mee. Meee., (8888) 88, 8888. |
[37] | Meeee, M.; Meeeee, M.; Meeeee, M., Mee. Meee., (8888) 88, 8888. |