Feng-Kai Guo: Frontiers Science Center for New Organic Matter, the State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. ORCID
Yi-Lin Lu: Frontiers Science Center for New Organic Matter, the State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Ming-Yao Huang: Frontiers Science Center for New Organic Matter, the State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. ORCID
Ji-Min Yang: Frontiers Science Center for New Organic Matter, the State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. ORCID
Jia-Lei Guo: Frontiers Science Center for New Organic Matter, the State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Zi-Yi Wan: Frontiers Science Center for New Organic Matter, the State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Shou-Fei Zhu: Frontiers Science Center for New Organic Matter, the State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China. ORCID
The Wittig reaction, which is one of the most effective methods for synthesizing alkenes from carbonyl compounds, generally gives thermodynamically stable -alkenes, and synthesis of trisubstituted -alkenes from ketones presents notable challenges. Here, we report what we refer to as Wittig/B���H insertion reactions, which innovatively combine a Wittig reaction with carbene insertion into a B���H bond and constitute a promising method for the synthesis of thermodynamically unstable trisubstituted -boryl alkenes. Combined with the easy transformations of boryl group, this methodology provides efficient access to a variety of previously unavailable trisubstituted -alkenes and thus provides a platform for discovery of pharmaceuticals. The unique selectivity of the reaction is determined by the maximum overlap of the orbitals between the B���H bond of the borane adduct and the alkylidene carbene intermediate in the transition state.
References
Angew Chem Int Ed Engl. 2007;46(39):7506-8
[PMID: 17705207]
