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Chem Commun (Camb). 2017 Mar 28;53(26):3721-3724. doi: 10.1039/c7cc00005g.

Tertiary amine self-catalyzed intramolecular Csp3-H functionalization with in situ generated allenes for the formation of 3-alkenyl indolines.

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Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China.


A novel methodology for the synthesis of 3-alkenyl indolines through the reaction of in situ generated allenes with N-benzylic Csp3-H has been developed. The reaction was realized by Pd(0) catalyzed allenylation of propargyl carbonate with organoboron and subsequent tertiary amine self-catalyzed Csp3-H functionalization in a one-pot process. Control reactions suggested that the substrate itself might also serve as a Lewis base for the N-benzylic Csp3-H functionalization.


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