Pedro J. Campos

Phase transfer catalysis and homogeneous reactions with β-oxyalkyl radicals from organomercurials

Abstract β-Alkoxy- and β-hydroxyalkyl radicals generated by sodium borohydride reduction of oxymercurials react with electron deficient olefins to give addition compounds in an homogeneous process. Heterogeneous reactions are also successful in the presence of catalytic amounts of surfactants and provide a superior method for the “one pot” reductive alkylation of oxymercurials.

A new electrophilic addition to acetylenes. Synthesis of 1,2-iodofunctionalized olefins

Abstract Acetylenes react with bis(pyridine)iodo(I) tetrafluoroborate ( 1 ) in the presence of a wide variety of nucleophiles (F, Cl, Br, I, SCN, pyridine, OAc, anisole, H) to give 1,2-iodofunctionalized olefins ( 4 ).

Iodo-carbofunctionalization of alkynes with aromatic rings and IPy2BF4

Abstract Alkynes react with bis(pyridine)iodine(I)tetrafluoroborate ( 1 ) and aromatic rings (activated, nonactivated and deactivated) in a Friedel-Crafts-type alkylation reaction to give, in a regio and stereoselective way, trans -β-iodostyrene derivatives.

A new and versatile method for iodofunctionalization of 1,3-dienes

Abstract We wish to report the reactions of conjugated dienes with I(py) 2 BF 4 . This simple and general method allows the regiospecific 1,2-addition of iodine and a nucleophile to terminal dienes and the 1,4-addition to internal dienes.

Synthesis of 2-functionalized 1-chloro-1-iodo-1-alkenes from 1-chloro-1-alkynes and IPy2BF4

Abstract 1-Chloro-1-alkynes react with bis(pyridine)iodine( I )tetrafluoroborate ( 1 ) and nucleophiles (AcOH, HCOOH, Cl, Br, I) to give, in a regio- and stereoselective addition, 2-functionalized 1-chloro-1-iodo-1-alkenes.

Iodofunctionalization of alkynylsulfides with IPy2BF4

Alkynylsulfides react with bis(pyridine)iodine (I) tetrafluoroborate (1) and nucleophiles in a regio-and stereoselective electrophilic addition reaction to give 1-functionalized 2-iodovinylsulfides.

1,4-regioselective iodofunctionalizations of 1,3-butadiene

Abstract Addition reactions of benzene and acetonitrile to 1,3-butadiene are described. This new iodofunctionalization process proceeds “via” iodonium ion-allylic cation equilibrium and gives regioselectively 1,4-adducts, which can be alternatively obtained by acid treatment of the 1,2-derivative 8 .