Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
7.4.4 Gold-Catalyzed Ring Opening (via Silaboration) of Oxetanes and Epoxides

DOI: 10.1055/sos-SD-230-00085

Pineschi, M.; Boldrini, C.Science of Synthesis: Advances in Organoboron Chemistry towards Organic Synthesis, (20191218.

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]

Meeeeeeeeee 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]

Meeeeeeeeee 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


Cookie-Einstellungen