Chiral Aniline Synthesis via Stereospecific C(sp3)–C(sp2) Coupling of Boronic Esters with Aryl Hydrazines | Zendy

Venkataraman Ganesh | Zendy; Adam Noble | Zendy; Varinder K. Aggarwal | Zendy

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Chiral Aniline Synthesis via Stereospecific C(sp³)–C(sp²) Coupling of Boronic Esters with Aryl Hydrazines

Author(s) -

Venkataraman Ganesh,

Adam Noble,

Varinder K. Aggarwal

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b02615

Subject(s) - chemistry , aryl , aniline , stereospecificity , acylation , bond cleavage , stereochemistry , boronic acid , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , alkyl

An enantiospecific coupling between alkylboronic esters and lithiated aryl hydrazines is described. The reaction proceeds under transition-metal-free conditions and is promoted by acylation of a hydrazinyl arylboronate complex, which triggers a N-N bond cleavage with concomitant 1,2-metalate rearrangement. Judicious choice of the acylating agent enabled the synthesis of ortho- and para-substituted anilines with essentially complete enantiospecificity from a wide range of boronic ester substrates.

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