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Please login to access the full content or check if you have access via 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]

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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]

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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.

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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]

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