Categories: C-C Bond Formation > Arenes, Cyclic Compounds > Benzocycloalkenes
Synthesis of indanes
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Recent Literature
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 mild and convenient free-radical cyclization of organohalides in the presence
of a NiCl2 • DME/Pybox complex as the catalyst and zinc powder in
methanol efficiently gives carbo-, oxa-, and azacycles as products in high
yields from unsaturated alkyl halides.
H. Kim, C. Lee, Org. Lett., 2011,
13, 2050-2053.
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.
A cationic rhodium(I)/BINAP complex-catalyzed decarboxylative [2 + 2 + 2]
cycloaddition of 1,6- and 1,7-diynes with commercially available vinylene
carbonate enables a new route to substituted phenols.
H. Hara, M. Hirano, K. Tanaka, Org. Lett., 2009,
11, 1337-1340.
A AuCl-catalyzed, flexible synthesis of highly substituted, benzyl-protected
phenols unites enal/enones and benzyl allenyl ethers in a [3+3] fashion in two
steps, allowing excellent control of substitution at the benzene ring.
X. Huang, L. Zhang, Org. Lett., 2007,
9, 4627-4630.
