Photoinduced Deaminative Borylation of Alkylamines

Jingjing Wu; Lin He; Adam Noble; Varinder K. Aggarwal

doi:10.1021/jacs.8b07103

Photoinduced Deaminative Borylation of Alkylamines

Jingjing Wu, Lin He, Adam Noble, Varinder K. Aggarwal^*

^*Corresponding author for this work

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

125 Citations (Scopus)

262 Downloads (Pure)

Abstract

An operationally simple deaminative borylation reaction of primary alkylamines has been developed. The formation of electron-donor-acceptor complexes between N-alkylpyridinium salts and bis(catecholato)diboron enables photoinduced single-electron transfer and fragmentation to carbon-centered radicals, which are subsequently borylated. The mild conditions allow a diverse range of readily available alkylamines to be efficiently converted into synthetically valuable alkylboronic esters under catalyst-free conditions.

Original language	English
Pages (from-to)	10700-10704
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	34
DOIs	https://doi.org/10.1021/jacs.8b07103
Publication status	Published - 29 Aug 2018

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10.1021/jacs.8b07103Licence: CC BY-NC

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1 Finished
1 Active

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K.
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.
14/05/12 → 13/01/18
Project: Research

Professor Varinder K Aggarwal
- V.Aggarwal@bristol.ac.uk
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
Person: Academic , Member
Dr Adam Noble
- a.noble@bristol.ac.uk
- School of Chemistry - Research Officer
Person: Academic

Cite this

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title = "Photoinduced Deaminative Borylation of Alkylamines",

abstract = "An operationally simple deaminative borylation reaction of primary alkylamines has been developed. The formation of electron-donor-acceptor complexes between N-alkylpyridinium salts and bis(catecholato)diboron enables photoinduced single-electron transfer and fragmentation to carbon-centered radicals, which are subsequently borylated. The mild conditions allow a diverse range of readily available alkylamines to be efficiently converted into synthetically valuable alkylboronic esters under catalyst-free conditions.",

author = "Jingjing Wu and Lin He and Adam Noble and Aggarwal, {Varinder K.}",

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AB - An operationally simple deaminative borylation reaction of primary alkylamines has been developed. The formation of electron-donor-acceptor complexes between N-alkylpyridinium salts and bis(catecholato)diboron enables photoinduced single-electron transfer and fragmentation to carbon-centered radicals, which are subsequently borylated. The mild conditions allow a diverse range of readily available alkylamines to be efficiently converted into synthetically valuable alkylboronic esters under catalyst-free conditions.

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ER -

Photoinduced Deaminative Borylation of Alkylamines

Abstract

Access to Document

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

Professor Varinder K Aggarwal

Dr Adam Noble

Cite this