781-33-9Relevant articles and documents
Synthesis of Allylboronates via Zweifel-type Deprotonative Olefination
Xu, Nuo,Xu, Jianeng,Zhu, Qing,Liu, Chao
, p. 2403 - 2407 (2020/12/30)
A method for the synthesis of allylboronates via Zweifel-type deprotonative olefination was demonstrated. Tetrasubstituted vinylboronates were used as the substrates. NCS (N-chlorosuccinimide) was used as a bifunctional additive, electrophile and base. This method exhibited a different elimination strategy in Zweifel type transformation to afford allylboronates. The homo-alcohols and alkenes were stereoselective synthesized from the obtained allylboronates, demonstrating the synthetic value of this methodology. (Figure presented.).
Method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins
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Paragraph 0054-0063; 0079-0081, (2021/02/06)
The invention discloses a method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins, wherein the method comprises the steps: carrying out hydrocarbylation reaction on the non-terminal olefins and sulfoxide in the presence of ferric salt and hydrogen peroxide, carrying out one-pot reaction on disubstituted non-terminal olefins to generate the trisubstituted olefins, and carrying out one-pot reaction on the trisubstituted non-terminal olefins to generate the tetrasubstituted olefins. In the method, sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefins, and one more hydrocarbyl substituent is added to a reaction product compared with a double-bond carbon atom of a reactant, so that an olefin carbon chain isincreased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.
Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate
Cao, Zhi-Chao,Xu, Pei-Lin,Luo, Qin-Yu,Li, Xiao-Lei,Yu, Da-Gang,Fang, Huayi,Shi, Zhang-Jie
supporting information, p. 781 - 785 (2019/06/24)
A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di- or tri- substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio- and stereo-selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.