Preparation of organotin reagents

Inter- and Intramolecular Radical Couplings of Ene-ynes or Halo-alkenes Promoted by an InCl3/MeONa/Ph2SiH2 System

“…The use of radical reactions in modern organic synthesis is now well-established . Despite the disadvantages of toxicity and difficulty in the removal of tin residues, the majority of examples still rely on the use of tri- n -butyltin hydride because of its high versatility. , An alternative promising radical reagent, dihalogenoindium hydride (HInX 2 ), has been recently found by us and other groups and can be generated from indium(III) trihalides (InCl 3 or InBr 3 ) and metal hydrides. − At first, Bu 3 SnH had to be employed as a hydride source, and then it was replaced by NaBH 4 , DIBAL-H, and then Et 3 SiH . While the advances have been significant, all suffer from the strong reducing ability of the hydride sources themselves and from the actions of byproducts.…”

Triethylsilane−Indium(III) Chloride System as a Radical Reagent

“…The use of radical reactions in modern organic synthesis is now well-established . Despite the many well-documented advantages of free-radical chain reactions in organic chemistry, the majority of examples still rely on the use of tri- n -butyltin hydrides. , Hence, a major area of current research is the development of processes that seek to either alleviate the problems associated with toxic tin residues or remove the need for tin completely . With a potential similar to that of Bu 3 SnH, dihalogenoindium hydrides (X 2 InH) have been recently found by us and other groups to be novel reagents that were generated by the transmetalation of indium(III) trihalides (InCl 3 or InBr 3 ) with metal hydrides. − At first, Bu 3 SnH was employed as a hydride source, and then it was replaced by NaBH 4 6 and DIBAL-H .…”

Indium(III) Chloride−Sodium Borohydride System: A Convenient Radical Reagent for an Alternative to Tributyltin Hydride System

“…Among radical reducing reagents, tributyltin hydride (Bu 3 SnH) is the most useful one in intermolecular radical additions using alkyl halides and unsaturated compounds such as alkenes and alkynes because of the high kinetic balance of the steps of dehalogenation by tributyltin radical, addition of the resulting alkyl radical to unsaturated bond and hydrogen donation of tributyltin hydride .…”