Indium(III) chloride, anhydrous, 98+%, Thermo Scientific Chemicals

General References:

1. 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 halide in 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).
2. Promotes efficient azidolysis of ɑß-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).
3. In combination with a dithiol, catalyzes the efficient transthioacetalization of acetals to dithioacetals: Synlett, 727 (2002).
4. Aldoximes can be dehydrated to nitriles; ketoximes undergo the Beckmann rearrangement to amides: Chem. Commun., 1196 (2000).
5. Indium enolates are readily formed by transmetallation of Li enolates. These undergo Reformatsky-type reactions with aldehydes to give ß-hydroxy esters. ɑ-Bromo enolates give Darzens-type ɑß-epoxy carbonyl compounds: J. Chem. Soc., Perkin 1, 825 (2000).
6. Catalyst for conjugate addition of indoles to electron-deficient alkenes: Synthesis, 2165 (2001):
7. The combination with NaBH₄ has been reported to be an effective radical reducing system, replacing the environmentally unfavorable TBTH (Tri-n-butyl tin hydride, A13298), e.g. in dehalogenation and cyclization reactions: J. Am. Chem. Soc., 124, 906 (2002).
8. In combination with Triethyl silane, A10320 and a radical initiator, generates a radical reagent, analogous to Tri-n-butyl tin hydride, A13298: Org. Lett., 6, 4981 (2004).