Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds | Zendy

Josep Llaveria | Zendy; Daniele Leonori | Zendy; Varinder K. Aggarwal | Zendy

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Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

Author(s) -

Josep Llaveria,

Daniele Leonori,

Varinder K. Aggarwal

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b07842

Subject(s) - chemistry , stereospecificity , boronic acid , coupling (piping) , combinatorial chemistry , suzuki reaction , oxidative coupling of methane , stereochemistry , organic chemistry , catalysis , palladium , mechanical engineering , engineering

A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition of Troc-Cl, which activates the nitrogen and induces 1,2-migration. Oxidative workup furnishes the coupled product with >98% es.

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