Categories: C-C Bond Formation > Arenes, Cyclic Compounds > Benzocycloalkenes
Synthesis of benzocyclobutenes
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Recent Literature
A combination of Pd(OAc)2 and PtBu3 as catalyst, K2CO3
as the base, and DMF as solvent allows the synthesis of benzocyclobutenes (BCB)
by C-H activation of methyl groups. Various substituted BCBs were obtained under
these conditions with good yields, including molecules that are hardly
accessible by other methods.
M. Chaumontet, R. Piccardi, N. Audic, J. Hitce, J.-L. Peglion, E. Clot, O.
Baudoin, J. Am. Chem. Soc., 2008,
130, 15157-15166.
A new, mild, one-pot zirconium-promoted cross-coupling reaction of aryllithium
compounds and alkenyl bromides allows the regio- and diastereoselective
synthesis of functionalized cyclobutabenzene derivatives from simple and easily
available starting materials.
J. Barluenga, J. Calleja, M. J. Antón, L. Álvarez-Rodrigo, F. Rodríguez, F. J.
Fañanás, Org. Lett.,
2008,
10, 4469-4471.
The photocatalytic reactions of benzoylformate esters with alkenes can be
directed toward either Paternò-Büchi cycloadditions or allylic functionalization
reactions under conditions favoring energy transfer or electron transfer,
respectively.
J. Zheng, X. Dong, T. P. Yoon,
Org. Lett., 2020, 22, 6510-6515.
Benzyne-[2+2] cycloadditions with enamides enabled the development of a highly
stereoselective tandem [2+2] cycloaddition-pericyclic
ring-opening-intramolecular-N-tethered-[4+2] cycloaddition for rapid
assembly of nitrogen heterocycles.
J. B. Feltenberge, R. Hayashi, Y. Tang, E. S. C. Babiash, R. P. Hsung, Org. Lett., 2009,
11, 3666-3669.