| Polysubstituted silyl heterocyclic compounds are important and versatile intermediates in the synthesis of various functional molecules or biologically attractive molecules due to their unique properties.They have great application value and development potential in the fields of molecular skeleton construction,functional materials and pharmaceutical synthesis.In recent years,numerous methods have been established to synthesize silyl heterocyclic compounds.These methods mainly include benzoheterocycle silylation,multi-step coupling cyclization,multi-component one-pot reactions and some other reactions.Although each approach has its own advantages,some limitations and shortcoming still exist,including use of heavy metal catalysts,harsh reaction conditions,low regioselectivity and difficult preparation of starting materials.Hence it is necessary to develop economic and efficient strategy for the synthesis of silyl heterocyclic compounds.Startingfromsubstitutedo-（1-alkynyl）（thio）anisolesor o-（1-alkynyl）-N-methylaniline and silane,a one-pot protocol for the construction of silyl heterocyclic compounds has been developed via C–X bond cleavage and C–X/C–Si bond formation under the catalysis of B（C6F5）3 at 120 oC.This paper is mainly discussed from three parts:Part Ⅰ,the synthesis progress of C–Si construction is reviewed.Organosilicon compounds containing C–Si bonds are widely used in the synthesis of many drug molecules,biologically active molecules and material molecules due to their unique physical and chemical properties.This part mainly starts from C（sp）–Si,C（sp2）–Si and C（sp3）–Si,and summarizes the advantages and disadvantages,mechanism and research significance of such reactions.Part Ⅱ,in view of the important role of heterocyclic compounds in the field of chemical synthesis,the application of 2-alkynyl（thio）anisole/2-alkynylaniline in the construction of polysubstituted benzoheterocyclic compounds is comprehensively described.In addition,the synthetic methods of silyl substituted heterocyclic compounds are summarized.Part Ⅲ,a novel synthetic method of 3-silyl heterocyclic compounds is described.The main contents of this study include four parts.1)The conditions for the synthesis of 3-silyl heterocyclic compounds were first explored,and the optimal reaction conditions were carried out using B（C6F5）3（15 mol%）in Ph Cl at 120 oC under N2 atmosphere.2)36 substituted o-（1-alkynyl）（thio）anisoles or o-（1-alkynyl）-N-methylanilines were examined under the optimal reaction conditions,and the desired products were obtained in moderate to good yields with high regioselectivity.3)To demonstrate the synthetic value of this method,we investigated further derivation experiments to form diverse heterocyclic compounds by3-silylbenzo[b]thiophenes.4)A plausible reaction mechanism for the B（C6F5）3-catalyzed silylation is proposed on the basis of mechanism study. |
