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

Venkataraman Ganesh; Adam Noble; Varinder K. Aggarwal

doi:10.1021/acs.orglett.8b02615

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

Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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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 language	English
Pages (from-to)	6144-6147
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	19
Early online date	17 Sept 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02615
Publication status	Published - 5 Oct 2018

Research Groups and Themes

Organic & Biological

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Newton Fellowship - Dr Ganesh Venkataraman
Aggarwal, V. K. (Principal Investigator)
4/01/16 → 3/01/18
Project: Research
FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research

Cite this

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title = "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.",

author = "Venkataraman Ganesh and Adam Noble and Aggarwal, \{Varinder K.\}",

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AU - Noble, Adam

AU - Aggarwal, Varinder K.

PY - 2018/10/5

Y1 - 2018/10/5

N2 - 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.

AB - 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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DO - 10.1021/acs.orglett.8b02615

M3 - Article (Academic Journal)

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IS - 19

ER -

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

Abstract

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Projects

Newton Fellowship - Dr Ganesh Venkataraman

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this