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Copper-catalyzed borylative couplings with C−N electrophiles

Copper-catalyzed borylative couplings with C−N electrophiles
Copper-catalyzed borylative couplings with C−N electrophiles

Copper-catalyzed borylative multicomponent reactions (MCRs) involving olefins and C−N electrophiles are a powerful tool to rapidly build up molecular complexity. The products from these reactions contain multiple functionalities, such as amino, cyano and boronate groups, that are ubiquitous in medicinal and process chemistry programs. Copper-catalyzed MCRs are particularly attractive because they use a relatively abundant and non-toxic catalyst to selectively deliver high-value products from simple feedstocks such as olefins. In this Minireview, we explore this rapidly emerging field and survey the borylative union of allenes, dienes, styrenes and other olefins, with imines, nitriles and related C−N electrophiles.

borocupration, copper, imine, multicomponent reaction, nitrile
1433-7851
20278-20289
Talbot, Fabien J.T.
fc968b03-833f-4fc6-b6bd-4771170a7458
Dherbassy, Quentin
84c92592-f8db-4811-a5ad-f717d554713e
Manna, Srimanta
79e58031-758a-42ae-9110-5ceec8a2f9e9
Shi, Chunling
bbedbddc-883f-4d1a-a678-67a0fd6fa33d
Zhang, Shibo
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Howell, Gareth P.
456b4301-dc69-4be0-a6d3-9b3dc2d69d0c
Perry, Gregory J.P.
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Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
Talbot, Fabien J.T.
fc968b03-833f-4fc6-b6bd-4771170a7458
Dherbassy, Quentin
84c92592-f8db-4811-a5ad-f717d554713e
Manna, Srimanta
79e58031-758a-42ae-9110-5ceec8a2f9e9
Shi, Chunling
bbedbddc-883f-4d1a-a678-67a0fd6fa33d
Zhang, Shibo
d7b2db9e-83bb-44b5-b59a-ccc6374e953e
Howell, Gareth P.
456b4301-dc69-4be0-a6d3-9b3dc2d69d0c
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4

Talbot, Fabien J.T., Dherbassy, Quentin, Manna, Srimanta, Shi, Chunling, Zhang, Shibo, Howell, Gareth P., Perry, Gregory J.P. and Procter, David J. (2020) Copper-catalyzed borylative couplings with C−N electrophiles. Angewandte Chemie - International Edition, 59 (46), 20278-20289. (doi:10.1002/anie.202007251).

Record type: Review

Abstract

Copper-catalyzed borylative multicomponent reactions (MCRs) involving olefins and C−N electrophiles are a powerful tool to rapidly build up molecular complexity. The products from these reactions contain multiple functionalities, such as amino, cyano and boronate groups, that are ubiquitous in medicinal and process chemistry programs. Copper-catalyzed MCRs are particularly attractive because they use a relatively abundant and non-toxic catalyst to selectively deliver high-value products from simple feedstocks such as olefins. In this Minireview, we explore this rapidly emerging field and survey the borylative union of allenes, dienes, styrenes and other olefins, with imines, nitriles and related C−N electrophiles.

Text
Angew Chem Int Ed - 2020 - Talbot - Copper‐Catalyzed Borylative Couplings with C N Electrophiles - Version of Record
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Accepted/In Press date: 16 June 2020
e-pub ahead of print date: 28 July 2020
Additional Information: Funding Information: We thank AstraZeneca (CASE Studentship to F.J.T.T.), EPSRC (Studentship to F.J.T.T. and Established Career Fellowship to D.J.P.; EP/M005062/1), SCI (Scholarship to F.J.T.T.), Jiangsu Oversea Visiting Scholar Program for University Prominent Young & Middle‐aged Teachers and Presidents (Funding to C.S.), the Leverhulme Trust (PDRA to Q.D.; RPG‐2016‐360), the European Union Horizon 2020 (Fellowship to S.M.; Marie Sklodowska‐Curie grant 798846‐CuCAN) and the University of Manchester (Lectureship to G.J.P.P. Fabien Talbot received his BSc from the University of Angers (France) with one year spent at the University of Strathclyde (UK). He then undertook an MSc at the University of Strasbourg (France) and did his research project at the University of Manchester (UK) working on nickel catalysis in Prof. David Procter's research group. In 2017 he stayed in the Procter group for a PhD funded by AstraZeneca and the EPSRC. He is also the recipient of an SCI Scholarship. His research aims to develop new copper‐catalyzed processes
Keywords: borocupration, copper, imine, multicomponent reaction, nitrile

Identifiers

Local EPrints ID: 478109
URI: http://eprints.soton.ac.uk/id/eprint/478109
ISSN: 1433-7851
PURE UUID: ada48439-f49d-4a9f-9fd0-c55b59ed757b
ORCID for Gregory J.P. Perry: ORCID iD orcid.org/0000-0001-8173-3369

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Date deposited: 21 Jun 2023 17:00
Last modified: 06 Jun 2024 02:17

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Contributors

Author: Fabien J.T. Talbot
Author: Quentin Dherbassy
Author: Srimanta Manna
Author: Chunling Shi
Author: Shibo Zhang
Author: Gareth P. Howell
Author: Gregory J.P. Perry ORCID iD
Author: David J. Procter

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