Manganese(I)‐Catalyzed Regioselective C−H Allenylation: Direct Access to 2‐Allenylindoles | Zendy

Lu Qingquan | Zendy; Greßies Steffen | Zendy; Klauck Felix J. R. | Zendy; Glorius Frank | Zendy

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Manganese(I)‐Catalyzed Regioselective C−H Allenylation: Direct Access to 2‐Allenylindoles

Author(s) -

Lu Qingquan,

Greßies Steffen,

Klauck Felix J. R.,

Glorius Frank

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201701767

Subject(s) - regioselectivity , manganese , catalysis , chemistry , computer science , combinatorial chemistry , organic chemistry

A Mn I ‐catalyzed regioselective C−H allenylation is reported that allows a broad range of 2‐allenylindoles to be synthesized regioselectively on a gram scale under simple conditions. Notably, a highly efficient chirality transfer was observed (up to 93 % ee ) in this transformation. This procedure was further found to allow, for the first time, the direct preparation of ketones by Mn I ‐catalyzed C−H activation. Mechanistic investigations revealed that the precoordination of the oxygen atom to the manganese center as well as the congested tertiary carbon atom in the propargylic carbonates play a crucial role.

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