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47.3.1.1.2.4 Variation 4: With Organosilicon and Organotin Compounds

DOI: 10.1055/sos-SD-047-00558

Roy, K.-M.Science of Synthesis, (2010471142.

Carboncarbon bond-forming reactions using organosilicon or organotin reagents are the subject of numerous reports regarding the synthesis of nonconjugated dienes. Coupling reactions using various organosilicon compounds are usually performed in the presence of a catalyst. Thus, acetylenes are converted regio- and stereoselectively in moderate yields into E-1,4-dienes by palladium-catalyzed coupling of allylic substrates with alkenylpentafluorosilicates, which are derived by hydrosilylation of a terminal alkyne and subsequent treatment with potassium fluoride.[‌35‌] A palladium catalyst is also used in cross-coupling reactions of alkenylfluorosilanes with allylic carbonates to give 1,4-dienes with retention of configuration.[‌36‌] In a different approach, ruthenium-catalyzed Alderene reactions of (benzyldimethylsilyl)alkynes with alkenes afford benzyldimethylsilyl-substituted 1,4-dienes, which can be further elaborated by cross-coupling reactions.[‌37‌]

Meeeeeeee eeeeeeeeeeeeee 88 eee 88 eeee eeee eeeeeeee ee eeeeeee eeeeeeeee eeeee-eeeeeeee eeeeeeeee eeee eeeeeeeeeeeeeeeeeeeee eeee ee 88 ee eee eeeeeeee ee eee(MM) eeeeeeee ee eeee 8,8-eeeeee eeee ee 88, 88, eee 88 ee eeee eeeeee (Meeeee 88). Meeeeee eeeeeeeeeeeeee eee eeee eeeeeeee ee eeeee eeeeeeeee, eee eeeeeeeeeeee ee e eeeeeeeeeeeeee eeeee ee eee γ-eeeeeeee eeeeeeeeee eeeeeeeee eee eeeeeeeeee. Meeee eee eeeeeeeeeeeeee eeeee eee ee eeeeeee ee eeeeeeeee ee eeeeeeeeeee ee eeeeeeeeee, eee eeeeee eeeeee e eeeeeeeeeeeeee eeeeee ee 8,8-eeeeee.[‌88‌] Me e eeeeeee eeeeeeee, 8,8-eeeeee eee eeeeeeee ee eeee eeeeee ee eeeeeeee eeeeeeeeeeeeeeeeeeeee eeee eeeeeee, eeeeeeeee, eee eeeeeeee eeeee eeeeeeeeeeeeee eeeeee ee eee eeeeeeee ee eeee(MM) eeeeeeee ee e Meeee eeee.[‌88‌]

Meeeee 88 Meeee Meeeeeee ee Meeeeeeeeeeeee eeee Meeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeee (88/88) Meeee (%) Mee
Me M M M 88:88 88 [‌88‌]
Me M M Me 88:88 88 [‌88‌]
Me Me Me M 888:8 88 [‌88‌]
Me M M M 88:88 88 [‌88‌]
Me M M Me 88:88 88 [‌88‌]

Meeeeeeee eeeeeeee eee eeeee eee eeee eeeeeeeee eeeeeeeeeeeeee eeeeeeee, eeeeeee eeee eee ee eeeeeeee eeeeee ee eeeeeee eeeeeeee eeeee, eee eeeeeeeeeeeeeee eee eee eee-eeeeeeeee. Meeeeeeee, e eeeeee ee 8,8- eee 8,8-eeeeee eeee eeee eeeeeeeeeee ee eeeee-eeeeeeee eeeeeeeee eeeee eeeeeeeeee eeeeeeee. Mee eeeeeee, 8,8-eeeeee eee eeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeeeeeee eeee e eeeeeeee-8-eeee eeeeeeeeeeeeeeeeeeeeeeeee ee eeee e eeeee eeeeeeee eeee (Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeee ee Meeee Meeeeeee ee Meeeeeeeeeeeeeeeeeeee[‌88‌,‌88‌]

Me e eeee eeeeeee eeeeeeee, eeeeeee eeeeeeeeee eee eeeee eeeeeee eeee eeeeeeee eeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeeeee ee eeee eeeeeee 8,8-eeeeee (Meeeee 88).[‌88‌‌88‌] Me eeeeeeee, eeeeeeeee-eeeeeeeee eeeee eeeeeeeee ee eeeeeeeeeeeeee eeee eeeeeeeeeeeeee eeee eee 8,8-eeeeee 88 eeeeeeeeeeeeeeeee ee eeee eeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeee Meeeeeee ee Meeeeee Meeeeeeeee eeee Meeeeeee Meeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 M8 M Meeeeeeeee Meeee (%) Mee
M M Me Me Me M Me MeMe8(MMMe)8, MMM, Me8M, MMMe8 88e [‌88‌]
Me Me Me M Me Me Me MeMe8(MMMe)8, MMM, Me8M, MMMe8 8888e [‌88‌]
Me M Me M M M Me Me8(eee)8, eee-8-eeeeeeeeeeeeee, MeMe, MMM 88 [‌88‌]
(MM8)8MM=MMe8 Me Me M M M MMe Me8(eee)8, MeMe, MMM 88 [‌88‌]
Me (MM8)8MM=MMe8 Me M M M MMe Me8(eee)8, MeMe, MMM 88 [‌88‌]
Me M Me M Me M MMe Me8(eee)8, MeMe, MMM 88 [‌88‌]

e MMM eeeee.

Meeeee 88 Meeee Meeeeeee ee Meeeeeeeeeeeee eeee Meeeeeeeeeeeee[‌88‌]

Mee eeeeeeeee ee 8,8-eeeeee eee ee eeeeeeee ee eeeeeee eeeeeeeeee eeeeeeee eeeeeeeeee eeeeeee eeeee eeeeeeee ee eeeeeee eee eeeeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee ee eeee eeeeeeee.[‌88‌,‌88‌,‌88‌] Meee, eeeeeeeeeeeeeee eeeeeeeeeee eee(eeeeeeeeeeeeee) eeeeeeeee, eeeeeeee ee eeeeeeee ee eeeeeee Meeeeeee (ee. Meeeeee 88.8.8.8.8.8) ee eeeeeeee(eeeee)eee eeeeeeee ee ee eeeeeeeeeeeeee eeeeeeee eeeeeee, eeee eeeeeeee eeeeee ee eee eeeeeeeeeeeee 8,8-eeeeee 88 (Meeeee 88).[‌88‌] Meeeeeee eeeeeee (88) eeeeeee eeee eeeeeeee eeeeeeee ee eee eeeeeeee ee e eeeeeeeee(8) eeeeeeee ee eeee eeeeee-eeeeeeeeeee 8,8-eeeeee 88 (Meeeee 88).[‌88‌] Meeeeeee ee eeeeee eee eeeeeee eeeeeeee 88 eeee eeeeeeeeeeeeeeeeee (88) eee eeeeeeeee eeee(MM) eeeeeeee eeeeeeee eeeeeeeeeeeeeeeee, eeeeeee eee eeeeeeee eeeeeeee 88 ee eeee eeeeee (Meeeee 88).[‌88‌] Meeeeeeeeee, eee eeeeeee eeeeeee eee β-eeeeeeeee eee eeeeeeeeeee ee eeeee-eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeee(MM) eeeeeeee ee e Meeee eeee eeeeeeee.[‌88‌]

Meeeee 88 MeeeeMeeee Meeeeeee Meeee Meeeeeee Meeeeeee[‌88‌]

Meeeee 88 Meeeeeee ee Meeeeeee Meeeeee eeee Meeeeeee Meeeeeee[‌88‌]

Meeeee 88 Meeeeeee ee Meeee Meeeeeee eeee Meeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeee-eeeeeeeee eeeeeeee ee e eeeeeee eeeeee eeeeeeeeee ee e eeeee eeeeeee, eeeeeeeeeeeeeeeeeeeee, eee eeeeeeeeee eeeeeeee eee eee-eee-8,8-eeeeeeeeeeeeeeeeee 88 ee eee eeee eeeeeeee. Meeeeeeee, 8,8,8,8-eeeeeeeeeeeeeeeeeeee (88) ee eeeeeeee eeee eeeeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee Meeee-Meeeeeeeeee Meeeeeeeeee[‌88‌]

Meee-eeeeeeeeeee eeeeeee eeeeeee eee eeeeeeee eee eeeeeeee ee eeeeeee eeeeeeeee-eeeeeeeee eeeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeeeeee eeeeeeeee ee eeee ee ee eeeeeeeeeeeeeee eeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8,8-Meeeeeeee-8-(8-eeeeeeeeeee)eeeee-8,8-eeeee (88, M8=Me; M8=M8=Me; M8=M); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eee eeeeeeee 88 (M8=Me; 888ee, 8.8eeee) ee MM8Me8 (8eM) eee eeeee e MM8Me8 eeeee eeee ee 88 (M8=M8=Me; M8=M; 8.8eM, 8eeee). Mee eeeeeee eee eeeeee ee 88°M, eee e eeee ee MeMe8 (8.8eeee) ee MM8Me8 (8.8eM) eee eeeee. Meeee eeeeeeee ee 88°M eee 8e, eee eeeeeeee eee eeeeeeee ee eeeeeeee ee M8M, eee eee eeeeeee eeeeeeeee eeee eeeeeeeee eeee MM8Me8. Mee eeeeeee eee eeeeee eeee 88% ee MM eee eeeee (Me8MM8), eeee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeeeee ee eee eeeeeee (eeeeee eee, eeeeeee) eeee eee eeeeeee; eeeee: 888ee (88%).

References


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