17791-25-2Relevant articles and documents
Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation
Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
supporting information, p. 2498 - 2504 (2021/04/13)
The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.
Ketone Synthesis by Direct, Orthogonal Chemoselective Hydroacylation of Alkenes with Amides: Use of Alkenes as Surrogates of Alkyl Carbanions
Geng, Hui,Huang, Pei-Qiang
supporting information, (2019/07/08)
Direct functionalization of alkenes and direct transformation of carboxamides are two exciting areas that have attracted considerable attention in recent years. We report herein that secondary amides, the least reactive derivatives of carbonyl compounds, upon activated with triflic anhydride, can serve as effective hydroacylating reagents in partner with alkenes to yield ketones at ambient temperature. The method was applied to the one-step synthesis of racemic dihydro-ar-turmerone. In this method, alkenes serve as surrogates of organometallic reagents, which allows the orthogonal chemoselective reactions. The ready availability of many olefins such as camphene and norbornene permits one-step ketone synthesis that would require several steps by conventional methods.
Decarboxylative Csp3-Csp3 coupling for benzylation of unstable ketone enolates: Synthesis of: P -(acylethyl)phenols
Wang, Sasa,Chen, Xinzheng,Ao, Qiaoqiao,Wang, Huifei,Zhai, Hongbin
supporting information, p. 9454 - 9457 (2016/07/29)
A new decarboxylative Csp3-Csp3 coupling approach for the benzylation of ketone enolates has been developed. A variety of raspberry ketone derivatives were conveniently synthesized in good to excellent yields under mild conditions. A crossover reaction shed light on the mechanism of this tandem reaction.