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

Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)
186 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)6144-6147
Number of pages4
JournalOrganic Letters
Volume20
Issue number19
Early online date17 Sep 2018
DOIs
Publication statusPublished - 5 Oct 2018

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