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

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.

SUBMITTER: Ganesh V

PROVIDER: S-EPMC6178205 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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

Ganesh Venkataraman V Noble Adam A Aggarwal Varinder K VK

Organic letters 20180917 19

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 ...[more]

PMID: 30221524

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