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Please login to access the full content or check if you have access via7.4.4 Gold-Catalyzed Ring Opening (via Silaboration) of Oxetanes and Epoxides
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Pineschi, M.; Boldrini, C., Science of Synthesis: Advances in Organoboron Chemistry towards Organic Synthesis, (2019) 1, 218.
Oxetanes (e.g., 85) and epoxides (e.g., 88) undergo a silaboration reaction catalyzed by titanium(IV) oxide supported gold nanoparticles (Scheme 24).[23] The reaction proceeds smoothly in 1,2-dichloroethane at 60 °C using 2-[dimethyl(phenyl)silyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (86) as reagent. The outcome of the reaction suggests that the boron moiety acts as a nucleophile. No reaction between oxetanes 85 and 2-[dimethyl(phenyl)silyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (86) is observed employing homogeneous palladium, platinum, or gold catalysts.[23]
Meeeee 88 Meeeeeeeeeee ee Meeeeeee[88]
M8 | M8 | M8 | Meeee (%) | Mee |
---|---|---|---|---|
M | Me | Me | 88 | [88] |
M | M | M | 88 | [88] |
M | M | Me | 88 | [88] |
M | M | Me | 88 | [88] |
M | (MM8)8 | 88 | [88] | |
M | MM8MMe | Me | 88 | [88] |
M | MM8MMMMMM | Me | 88 | [88] |
M | MM8MMe | Me | 88 | [88] |
Me | M | M | 88 | [88] |
8-MM8M8 | M | M | 88 | [88] |
8-Mee | M | M | 88 | [88] |
Me | M | M | 88e | [88] |
e Meeeeeee ee e 88:88 eeeeeeeeeeeee eeeeeee.
Mee eeeeee eee 8,8-eeeeeeeeeeeeeee 88 eee eeeeeeeee eeee (Meeeee 88). 8-Meee-eeeeeeeeeee eeeeeeee 88 (M8 = eeee) eeee eeeeeeee eeeeeeeeeeeeeeee, eeeeeee 8-eeeee-eeeeeeeeeee eeee eeeeeee eeeeeeeeeeeee eeeeeeee. Meeeeeee, 8,8-eeeeeeeeeeeee eeeeeeee eeee ee eeeeeeeee ee eeeeeee eeeeeeee ee eee eeeeeeee ee eee eeee eeeeeeeeeeee eeeeeeee.[88]
Meeeeeeee eee eeeeeeee ee eeeeeeee eeeee eeeeeee eeeeeeeeee, eeeeeee eeeeeeeeeeeee, ee eeee ee eee- eee eeeeeeeeeeeeeeee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeee, ee eeee eeee- eee 8,8-eeeeeeeeeeeee eeeeeeee 88 eee eeeeeeee eee eee eeeeeeee, eeeeeeeee 8,8-eeeeeeeeeeeeeee 88 eee 88 (Meeeee 88).[88,88]
Meeeee 88 Meeeeeeeeeee ee Meeeeeee[88]
Meeee | M8 | M8 | Meeee (%) | Mee | |
---|---|---|---|---|---|
88 | 88 | ||||
8 | (MM8)8 | 88 | [88] | ||
8 | (MM8)8 | 88 | [88] | ||
8 | Me | Me | 88e | [88] | |
8 | Me | Me | 88e | [88] | |
8 | Me | M | 88 | 88 | [88] |
8 | Me | M | 88 | 88 | [88] |
e Mee eee-eeeeeee eee eeee ee eeeeeeeee; eeeeeee eeeee (eeeee/eeeeeee) 88:88.
e Mee eeeee-eeeeeee eee eeee ee eeeeeeeee; eeeeeee eeeee (eeeeeee/eeeee) 88:88.
Meeeeeee eeeeeeee eeeee eeeee-eeeeeeeeeeeeeee (Meeeee 88, eeeeeee 8 eee 8). Mee eeeeeeeee eee-8,8-eeeeeeeeeeeeeee (88, M8 = M8 = Me) eeeee e eeeee/eeeeeee eeeeeee eeee eee eeeee-eeeeee ee eee eeeee eeeeeee (Meeeee 88, eeeee 8), eeeeeee eeeee-8,8-eeeeeeeeeeeeeee (88, M8 = M8 = Me) eeeeee e eeeee/eeeeeee eeeeeee eeeeeeee eee eeeeeee-eeeeee (Meeeee 88, eeeee 8). Meeeee ee eeeeeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeee eeeeeeee (Meeeee 88, eeeeeee 8 eee 8).[88]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
8-[Meeeeeee(eeeeee)eeeee]-8,8,8,8-eeeeeeeeeee-8,8,8-eeeeeeeeeeeee (88; 88 ee, 8.8 eeee), eeeee 8,8-eeeeeeeeeeeeee (8.8 eM), eee Me/MeM8 (88 ee, 8.8 eee% Me) eeee eeeee ee e eeee eeeeeeeeee ee eeeeeee eeeeeeeee 88 (8.8 eeee). Mee eeeeeee eee eeeeeee ee 88 °M eee 8 e. Mee eeeeeeeee eeeeee eee eeeeeeee eeeeeee e eeeee eee ee eeeeee eee eeee eee eee ee MM8Me8. Mee eeeeeeee eee eeeeeeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee.
8,8-Meeeeeeeeeeeeee 88/88; Meeeeee Meeeeeeee:[88]
8-[Meeeeeee(eeeeee)eeeee]-8,8,8,8-eeeeeeeeeee-8,8,8-eeeeeeeeeeeee (88; 88 ee, 8.8 eeee), eeeee 8,8-eeeeeeeeeeeeee (8.8 eM), eee Me/MeM8 (88 ee, 8.8 eee% Me) eeee eeeee ee e eeee eeeeeeeeee ee eeeeeee 88 (8.8 eeee). Mee eeeeeee eee eeeeeee ee 88 °M eee 8 e. Mee eeeeeeeee eeeeee eee eeeeeeee eeeeeee e eeeee eee ee eeeeee eee eeee eee eee ee MM8Me8. Mee eeeeeeee eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee.
References
[23] | Meeeeeeeeeeeeeee, M.; Meeee, M.; Meeeeeeee, M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
[24] | Meeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |