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Categories: C-C Bond Formation > Arenes, Cyclic Compounds > Benzocycloalkenes

Synthesis of indanes

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A number of indenes have been prepared in good yields by treatment of o-bromobenzyl zinc bromide with various terminal and internal alkynes in the presence of a nickel catalyst. The nickel-catalyzed carboannulation reaction was successfully extended to the synthesis of indanes using acrylates and styrene instead of an alkyne.
R. Deng, L. Sun, Z. Li, Org. Lett., 2007, 9, 5207-5210.


A highly enantioselective, intramolecular arylcyanation of unactivated olefins via C-CN bond activation has been accomplished using a Ni(0) catalyst, BPh3 as co-catalyst, and TangPHOS as a chiral ligand. Two new C-C bonds and one quaternary carbon stereogenic center are generated in a single synthetic step, converting readily available benzonitriles into 1,1-disubstituted indanes in good yield.
M. P. Watson, E. N. Jacobsen, J. Am. Chem. Soc., 2008, 130, 12594-12595.


An enantioselective nickel-catalyzed Negishi cross-coupling of racemic secondary benzylic bromides and chlorides is described. The catalyst components are commercially available and air-stable, and the reaction is not highly oxygen- or moisture-sensitive.
F. O. Arp, G. C. Fu, J. Am. Chem. Soc., 2005, 127, 10482-10483.


A stereoselective sequence of a RhI-catalyzed conjugate addition of boronic acids to enones followed by a Michael cyclization gives 1,2,3-trisubstituted indans in a highly regio- and stereoselective fashion.
C. Navarro, A. G. Csák˙, Org. Lett., 2008, 10, 217-219.