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

School of Chemistry

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

314 Citations (Scopus)

612 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

Research Groups and Themes

Bristol BioDesign Institute

Keywords

synthetic biology

Access to Document

10.1021/jacs.8b07103Licence: CC BY-NC

Full-text PDF (accepted author manuscript)
This is the accepted author manuscript (AAM). The final published version (version of record) is available online via ACS at https://doi.org/10.1021/jacs.8b07103 . Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 883 KBLicence: CC BY-NC

http://pubs.acs.org/doi/10.1021/jacs.8b07103

Handle.net

Persistent link

Cite this

@article{ae89b18d981e40e5b225316eee2fb7b9,

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.",

keywords = "synthetic biology",

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

year = "2018",

month = aug,

day = "29",

doi = "10.1021/jacs.8b07103",

language = "English",

volume = "140",

pages = "10700--10704",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "34",

}

TY - JOUR

T1 - Photoinduced Deaminative Borylation of Alkylamines

AU - Wu, Jingjing

AU - He, Lin

AU - Noble, Adam

AU - Aggarwal, Varinder K.

PY - 2018/8/29

Y1 - 2018/8/29

N2 - 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.

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.

KW - synthetic biology

UR - http://www.scopus.com/inward/record.url?scp=85052318116&partnerID=8YFLogxK

U2 - 10.1021/jacs.8b07103

DO - 10.1021/jacs.8b07103

M3 - Article (Academic Journal)

C2 - 30091912

SN - 0002-7863

VL - 140

SP - 10700

EP - 10704

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 34

ER -

Photoinduced Deaminative Borylation of Alkylamines

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

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

Photoinduced Deaminative Borylation of Alkylamines

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

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

Profiles

Professor Varinder K Aggarwal

Dr Adam Noble

Cite this