New Organic Reactions Using Alkynyl Bromides

As an important intermediates and versatile building blocks in organicsysithesis, alkynyl bromindes as an easily prepared from terminal alkynes with NBS inalmost quantitative yields come to our sight. Recently, carbon–Hydrogen activation andcarbon–heteroatom carbon–carbon bonds formation are the central topics in chemicalcommunity and attract scientists in organic sysithesis, so we envisaged our researches inorganic reactions by using1-bromoalkynes. The following contents were included.(1) The Sequential Reactions of Tetrazoles with Bromoalkynes for the Synthesis of(Z)-N-(2-bromo-1-vinyl)-N-Arylcyanamides and2-Arylindoles:2-Arylindoles wereprepared by a sequential reaction of Agcatalyzed a-addition–Pd-catalyzed C–H bondfunctionalization of tetrazoles with bromoalkynes. A stereo-controlled Ag-catalyzedα-addition reaction of tetrazoles with bromoalkynes underwent smoothly to generate(Z)-N-(2-bromo-1-vinyl)-N-arylcyanamides, which were subsequently converted into2-arylindoles through an intramolecular cyclization by Pd-catalyzed direct C–H bondfunctionalizations.(2) KOAc-Promoted Alkynylation of α-C H Bonds of Ethers with Alkynyl Bromidesunder Transition-metal-free Conditions: A novel KOAc-promoted α-position C–Hactivation and alkynylation of ethers with alkynyl bromides to2-alkynyl ethers has beendeveloped under transition-metal-free and simple reaction conditions. In addition, thismethodology can also be extended to the vinylation of ethers with vinyl bromides inexcellent regio-and stereo-selectivity. A wide range of direct C(sp)–C(sp3) andC(sp2)–C(sp3) bonds has been formed through this protocol, offers a new and alternativeroute.(3) Silver-Catalyzed Functionalization of1-Bromoalkynes: Highly Regio-andStereoselective Synthesis of (Z)-β-Bromo-1-Phenylvinyl Benzoate: A newsilver-catalyzed highly regio-and stereoselective functionalization reaction of simplebromoalkynes was reported in which the (Z)-2-Bromo-1-Phenylvinyl Benzoatederivatives were formed efficiently. The resulting products were versatile intermediatesin organic synthesis.