A Study of BF 3 ‐Promoted  ortho  Lithiation of Anilines and DFT Calculations on the Role of Fluorine–Lithium Interactions | Zendy

Kessar Satinder V. | Zendy; Singh Paramjit | Zendy; Singh Kamal N. | Zendy; Bharatam Prasad V. | Zendy; Sharma Arvind K. | Zendy; Lata Sneh | Zendy; Kaur Amarjit | Zendy

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A Study of BF 3 ‐Promoted ortho Lithiation of Anilines and DFT Calculations on the Role of Fluorine–Lithium Interactions

Author(s) -

Kessar Satinder V.,

Singh Paramjit,

Singh Kamal N.,

Bharatam Prasad V.,

Sharma Arvind K.,

Lata Sneh,

Kaur Amarjit

Publication year - 2008

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.200705967

Subject(s) - metalation , lithium (medication) , fluorine , chemistry , medicinal chemistry , density functional theory , computational chemistry , group (periodic table) , inductive effect , organic chemistry , medicine , endocrinology

Director's cut : The poor directing ability of the dimethylamino group in directed ortho metalation is altered by complexation to BF 3 , which makes it more strongly activating than methoxy and chloro groups. DFT calculations of simplified lithiated intermediates reveal a small role of the inductive effect, but a distinctive F⋅⋅⋅Li interaction that leads to a F–Li distance which is remarkably similar to the C–Li distance.

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