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- W2949271683 abstract "An efficient catalytic system has been developed for the synthesis of benzocyclobutenes by C−H activation of methyl groups. The optimal conditions employed a combination of Pd(OAc)2 and PtBu3 as catalyst, K2CO3 as the base, and DMF as solvent. A variety of substituted BCB were obtained under these conditions with yields in the 44−92% range, including molecules that are hardly accessible by other methods. The reaction was found limited to substrates bearing a quaternary benzylic carbon, but benzocyclobutenes bearing a tertiary benzylic carbon could be obtained indirectly from diesters by decarboxylation. Reaction substrates bearing a small substituent para to bromine gave an unexpected regioisomer that likely arose from a 1,4-palladium migration process. The formation of this “abnormal” regioisomer could be suppressed by introducing a larger subsituent para to bromine. DFT(B3PW91) calculations on the reaction of 2-bromo-tert-butylbenzene with Pd(PtBu3) with different bases (acetate, bicarbonate, carbonate)..." @default.
- W2949271683 created "2019-06-27" @default.
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- W2949271683 date "2009-03-17" @default.
- W2949271683 modified "2023-10-17" @default.
- W2949271683 title "ChemInform Abstract: Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study." @default.
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- W2949271683 doi "https://doi.org/10.1002/chin.200911068" @default.
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