One-pot synthesis of telluroketene acetals and haloketene acetals using sp2 geminated hetero organobismetallic intermediates

A novel one-pot synthesis of 1,1-dihalo-1-alkenes and 1,1-bis(butyltelluro)-1-alkenes was developed from hydrozirconation of alkynylzinc bromide with Cp2Zr(H)Cl and subsequent capture of the Zn/Zr 1,1-heterodimetallo-1-alkene intermediates with halogen and tellurium electrophiles. These protocols, which include multiple reactions in a one-pot procedure, allow the preparation of the potentially useful haloketene acetals and telluroketene acetals from terminal alkynes, under mild conditions and in a good yield. (C) 2012 Elsevier Ltd. All rights reserved.