Bifunctional Silylene–Aminoborane Enables Cooperative Activation of Unsaturated Bonds and Access to Heteroatom‐Enriched Polycycle
Abstract
Abstract We report the synthesis and cooperative reactivity of a bifunctional silylene–aminoborane compound, 1‐Ph‐2‐ t Bu‐1 H ‐2,1‐benzazaborolyl‐(amidinato)silylene ( 1 ), designed to preserve the ambiphilicity of both functional units while preventing intramolecular deactivation. 1 engages in unprecedented multicomponent activations of unsaturated bonds, including alkynes and phosphaalkynes, to construct novel main‐group element embedded polycyclic frameworks. Reaction with alkynes led to rare main‐group elements enriched semibullvalenes via highly regioselective [2 + 2 + 1] cycloaddition. Notably, reaction with a phosphaalkyne induced a distinct S N Ar‐like B─C bond cleavage and formation of a B─N─Si─P‐embedded barrelene analogue. Structural and computational analyses revealed the synergistic multi‐site activation modes and reaction pathways.
Article Details
Authors (8)
Zheng Su
Tianjin Key Laboratory of Structure and Performance for Functional Molecules College of Chemistry Tianjin Normal University Tianjin 300387 China
Mingdong Zhong
Tianjin Key Laboratory of Structure and Performance for Functional Molecules College of Chemistry Tianjin Normal University Tianjin 300387 China
Xixi Meng
Tianjin Key Laboratory of Structure and Performance for Functional Molecules College of Chemistry Tianjin Normal University Tianjin 300387 China
Ren Gao
Jiancheng Li
Department of Chemistry, College of Science
Minyi Yuan
Tianjin Key Laboratory of Structure and Performance for Functional Molecules College of Chemistry Tianjin Normal University Tianjin 300387 China
Herbert W. Roesky
Institut für Anorganische Chemie Georg‐August‐Universität Göttingen Göttingen 37077 Germany
Shaoguang Zhang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University Beijing 100084 China