•
Catalyst for conjugate addition of indoles to electron-deficient alkenes: Synthesis, 2165 (2001):
• Indium enolates are readily formed by transmetallation of Li enolates. These undergo Reformatsky-type reactions with aldehydes to give ?-hydroxy esters. ɑ-Bromo enolates give Darzens-type ɑ?-epoxy carbonyl compounds: J. Chem. Soc., Perkin 1, 825 (2000).
• For a brief feature on InCl3, see: Synlett, 531 (2002). For reviews of the use of In compounds in organic synthesis, see: Eur. J. Org. Chem., 2347 (2000); J. Chem. Soc., Perkin 1, 3015 (2000).
• Promotes efficient azidolysis of ɑ?-epoxy carboxyl derivatives in water at pH 4, with results superior to Yb(OTf)3 or Sc(OTf)3: J. Org. Chem., 66, 3554 (2001).
• In combination with a dithiol, catalyzes the efficient transthioacetalization of acetals to dithioacetals: Synlett, 727 (2002).
• Aldoximes can be dehydrated to nitriles; ketoximes undergo the Beckmann rearrangement to amides: Chem. Commun., 1196 (2000).
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The combination with NaBH4 has been reported to be an effective radical reducing system, replacing the environmentally unfavorable TBTH (Tri-n-butyltin hydride, A13298), e.g. in dehalogenation and cyclization reactions: J. Am. Chem. Soc., 124, 906 (2002).•
In combination with Triethylsilane, A10320 and a radical initiator, generates a radical reagent, analogous to Tri-n-butyltin hydride, A13298: Org. Lett., 6, 4981 (2004).• Mild, water tolerant Lewis acid catalyst, e.g. in allylation reactions of sensitive aldehydes with allyltributyltin: J. Org Chem., 61, 105 (1996). The allylstannane can also be generated in situ from the allyl halidein water: Tetrahedron Asym., 7, 1535 (1996). Catalyzes the Mukaiyama aldol reaction, under either solvent-free conditions: Tetrahedron Lett., 39, 1579 (1998), or in water: Chem. Commun., 1819 (1996); 861 (1998); Tetrahedron Lett., 38, 3465 (1997).For Diels-Alder reactions in water, see: Chem. Commun., 2315 (1996).
Harmful (X)
Corrosive (C)
