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.
An intramolecular, Pd-catalyzed C-H alkylation of arenes and heteroarenes is
successful with various unactivated primary and secondary alkyl halides,
including those with β-hydrogens. The mild, catalytic reaction conditions are
highly functional group tolerant and facilitate access to a broad range of
synthetically and medicinally interesting carbocyclic and heterocyclic systems.
A. R. O. Venning, P. T. Bohan, E. J. Alexanian, J. Am. Chem. Soc., 2015,
137, 3731-3734.
An asymmetric Ni-catalyzed intramolecular reductive Heck reaction of
unactivated alkenes tethered to aryl bromides provides various benzene-fused
cyclic compounds bearing a quaternary stereogenic center in good to excellent
yields and high enantioselectivities. A mechanism involves an enantiodetermining
migratory insertion and a subsequent protonation with water or alcoholic
solvents.
F. Yang, Y. Jin, C. Wang,
Org. Lett., 2019, 21, 6909-6913.
A catalytic synthesis of cycloalkanols in the presence of N2O as
an oxygen transfer agent onto sp3-hybridized carbons of simple
precursors offers mild conditions and wide substrate scope. The reaction even
enables to access carbocyclic compounds in an enantioselective manner.
S. Ni, F. Le Vaillant, A. Mateos-Calbet, R. Martin, J. Cornella, J. Am. Chem. Soc.,
2022, 144, 18223-18228.
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 Pd-catalyzed C(sp3)-H functionalization/carbenoid insertion enables
the rapid synthesis of bicyclic frameworks, generating all-carbon quaternary
centers via multiple C-C bond formations in a straightforward manner.
Á. Gutiérrez-Bonet, F. Juliá-Hernández, B. de Luis, R. Martin, J. Am. Chem. Soc., 2016,
138, 6384-6387.
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.
Half-sandwich rare-earth complexes catalyze a diastereodivergent (3 + 2)
annulation of aromatic aldimines with alkenes via C-H activation to provide both
trans and cis diastereoisomers of multisubstituted 1-aminoindanes.
The reaction offers 100% atom efficiency, excellent diastereoselectivity, broad
substrate scope, and good functional group compatibility.
X. Cong, G. Zhan, Z. Mo, M. Nishiura, Z. Hou, J. Am. Chem. Soc.,
2020, 142, 5531-5537.
Half-sandwich rare-earth complexes catalyze a diastereodivergent (3 + 2)
annulation of aromatic aldimines with alkenes via C-H activation to provide both
trans and cis diastereoisomers of multisubstituted 1-aminoindanes.
The reaction offers 100% atom efficiency, excellent diastereoselectivity, broad
substrate scope, and good functional group compatibility.
X. Cong, G. Zhan, Z. Mo, M. Nishiura, Z. Hou, J. Am. Chem. Soc.,
2020, 142, 5531-5537.
A ligand-enabled nickel-catalyzed intramolecular hydroalkenylation of imines
with unactivated alkenes provides various five- and six-membered cyclic allylic
amines in high yields. The use of both wide-bite-angle diphosphine ligand and
Brřnsted acid is crucial for realizing the reaction.
W.-M. Feng, T.-Y. Li, L.-J. Xiao, Q.-L. Zhou, Org. Lett., 2021, 23,
7900-7904.
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.