Science of Synthesis

de Haro, T.; Garayalde, D.; Nevado, C., Science of Synthesis Knowledge Updates, (2012) 3, 171.

The direct addition of a stabilized carbon nucleophile to an unactivated alkene is a well-established method for the formation of C—C bonds in organic chemistry.[‌26‌] Traditionally, free radicals[‌27‌–‌31‌] and Lewis acid catalysts[‌32‌] have mediated this transformation, although their efficiency can be greatly enhanced by transition-metal catalysts.[‌33‌] Gold(I) and gold(III) complexes have been investigated in the hydroalkylation of alkenes using substrates such as β-diketones and β-keto esters, which can directly react through their enol form.

Mee eeeeeeeeeeeeee eeeeeeeeeeeeeee ee eeeeeee ‌8‌ eeee 8,8-eeeeeeeeee eeeeeeeee ‌8‌ eeeeeeeee ee e eeeeeee ee eeee(MMM) eeeeeeee (8 eee%) eee eeeeee(M) eeeeeeeeeeeeeeeeeeeeeeeee (88 eee%) eeeeeee ee eee eeee-eeeeeeee eeeeeeeee ee eee M(ee8)—M(ee8) eeee ee eeeeeeee ‌8‌ ee e eeeeeeeeeeeeee eeeeee.[‌88‌,‌88‌] Meeeeee eeeeeeeee eee ee eeeee ee eeeeeee, eeeeeee eeeeeeeeeee, eeeeee eeeeeeeeeee eeeeeee, eeeeee, eeeeeee, eee eeeeee eeee eeeeee ee eeeee ee ‌Meeeee 8‌.

‌Meeeee 8‌ Meeeeeee ee 8,8-Meeeeeeee ee Meeeeeeeeee Meeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 8‌

M8	M8	M8	Meeee (%)	Mee
M	Me	Me	88	[‌88‌]
		Me	88	[‌88‌]
(MM8)8MM=MM		Me	88	[‌88‌]
MM8(MM=MM)8		Me	88	[‌88‌]
(MM8)8M		Me	88	[‌88‌]

β-Meee eeeeee (e.e., ‌8‌ eee ‌8‌)[‌88‌] eee eeeeeee (e.e., ‌88‌)[‌88‌] eee ee eeeeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeeee eeeeeee, eeeeeeeee eeeeee eeeeeeeeeee eeeeeee (e.e., ‌8‌ eee ‌8‌) eee eeeeee eeeeeee (e.e., ‌88‌), eeeeeeeeeeee. Mee eeeeeeeee eeeeeee ee eeeeeeeee eeeeee eee eeee eeee eeeeeeeeeeeeeeeeeeeeee eeeeeeee eee eeeee-eeeeeeeeeeee. Meeeeeeeeeeee, β-eeee eeeeee (e.e., ‌8‌) eeeeee eeeeee M- ee M-eeeeeee eeeeee eeeeee eee eeee eeeeeeeeeeee ee eee eeeeee eeeeeeeeeee eeeeee (e.e., ‌8‌) ee e eeeeee eeeeeeeeeeee. Meeee eeeeeeeee eeee ee eeeeeee eee eeeeeeeeeeeeee Meeeeee eeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeee.[‌88‌] Me eeeeeeee ee eee eeee eeeeeeee eeeeeeeeee eeeeeeeeee ee ‌Meeeee 8‌, eee eeeeeeeeeeeeee eeeeeeeeeeeeeee ee eeeeeee ee eeee eeeeeeeee ee eeee(M) eeeeeeeee (e.e., ‌8‌ ee ‌8‌) eee eeeee eeeeeeee eeeeeeeeee eee eeeeeeee (‌Meeeee 8‌).

‌Meeeee 8‌ Meeeeeeeeeeeee Meeeeeeeeeeeeee ee β-Meee Meeeee eee Meeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 8‌

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee-8,8-eeeeee ‌8‌; Meeeeee Meeeeeeee:[‌88‌,‌88‌]

M eeee ee MeMe8 (8.888 eeee, 8.88 eeeee) eee MeMMe (8.888 eeee, 8.88 eeeee) eee eeeeeee ee MM8Me8 (8 eM) ee ee eee 8 e. Meee, eee 8,8-eeeeeeee ‌8‌ (8.8 eeee, 8.8 eeeee) eee eee eeeeee ‌8‌ (8.8 eeee, 8.8 eeeee) eeee eeeee eee eeeeeee eeee eeee 8 e eee eee eeeeeeeee eeee eee eeeeeee eeeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).

8-Meeeee-8-eeeeeeeeeeeeeee-8-eeee, e.e. ‌8‌; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee Me eeeeeee ‌8‌ (8.88 eeee, 8.88 eeeee) eee MeMMe (8.88 eeee, 8.88 eeeee) ee eeeeeee (8 eM), eee β-eeee eeeee (8.8 eeee, 8.8 eeeee) eee eeeee. Mee eeeeeee eee eeeeeee ee 88 °M eee 8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).

Meeeeeee 8-Meeeee-8-eeeeeeeeeeeeeeeeee-8,8-eeeeeeeeeeeee ‌88‌ [M = M(MM8Me)8] ee 8-Meeeee-8-eeeeee-8-eeeeeeeeeeeeeeee ‌88‌ (M = MMe); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee(M) eeeeeeeeeee ee eeeeeeeeeee eeeeeeeee eee eeeeee ee eeeeeee eeee eeeee eeeeeee.

M eeeeeee ee Me eeeeeee ‌8‌ (8.8888 eeee, 8.88 eeeee), MeMeM8 (8.8888 eeee, 8.88 eeeee), eee eee eeeeee ‌88‌ (8.88 eeee, 8.8 eeeee) ee eeeeeee (8.8 eM) eee eeeeeee ee 88 °M eeeee ee eeeee eeeeeeeeee eee 8.8 ee 88 e. Meee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).

References