Modular synthesis of stereodefined benzocyclobutene derivatives via sequential Cu- And Pd-catalysis
Modular synthesis of stereodefined benzocyclobutene derivatives via sequential Cu- And Pd-catalysis
Benzocyclobutenes (BCBs) are of growing interest in materials and medicinal chemistry, although general routes for their provision remain underexplored. A modular, divergent, and stereoselective Cu- and Pd-catalyzed assembly/cyclization sequence allows the synthesis of densely functionalized BCBs, from readily accessible imine, allene, and diboron precursors. Preliminary results have identified enantioselective conditions for our protocol and highlighted, for example, its applicability to the synthesis of BCB-containing peptides. By simple variation of experimental conditions or substrate modification, our strategy was expanded to deliver indoline and quinoline derivatives, suitable for further manipulations.
asymmetric, benzocyclobutenes, copper, indolines, palladium
14448-14455
Talbot, Fabien J.T.
fc968b03-833f-4fc6-b6bd-4771170a7458
Zhang, Shibo
d7b2db9e-83bb-44b5-b59a-ccc6374e953e
Satpathi, Bishnupada
53bbe1c3-69c0-49c7-9219-2399a2d52974
Howell, Gareth P.
456b4301-dc69-4be0-a6d3-9b3dc2d69d0c
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Crisenza, Giacomo E.M.
3543868c-2fb0-485d-b236-d76bff609e88
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
3 December 2021
Talbot, Fabien J.T.
fc968b03-833f-4fc6-b6bd-4771170a7458
Zhang, Shibo
d7b2db9e-83bb-44b5-b59a-ccc6374e953e
Satpathi, Bishnupada
53bbe1c3-69c0-49c7-9219-2399a2d52974
Howell, Gareth P.
456b4301-dc69-4be0-a6d3-9b3dc2d69d0c
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Crisenza, Giacomo E.M.
3543868c-2fb0-485d-b236-d76bff609e88
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
Talbot, Fabien J.T., Zhang, Shibo, Satpathi, Bishnupada, Howell, Gareth P., Perry, Gregory J.P., Crisenza, Giacomo E.M. and Procter, David J.
(2021)
Modular synthesis of stereodefined benzocyclobutene derivatives via sequential Cu- And Pd-catalysis.
ACS Catalysis, 11 (23), .
(doi:10.1021/acscatal.1c04496).
Abstract
Benzocyclobutenes (BCBs) are of growing interest in materials and medicinal chemistry, although general routes for their provision remain underexplored. A modular, divergent, and stereoselective Cu- and Pd-catalyzed assembly/cyclization sequence allows the synthesis of densely functionalized BCBs, from readily accessible imine, allene, and diboron precursors. Preliminary results have identified enantioselective conditions for our protocol and highlighted, for example, its applicability to the synthesis of BCB-containing peptides. By simple variation of experimental conditions or substrate modification, our strategy was expanded to deliver indoline and quinoline derivatives, suitable for further manipulations.
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More information
e-pub ahead of print date: 16 November 2021
Published date: 3 December 2021
Additional Information:
Funding Information:
We thank AstraZeneca (CASE Studentship to F.J.T.T.), EPSRC (Studentship to F.J.T.T.), SCI (Scholarship to F.J.T.T.), the Marie Skłodowska-Curie Actions (H2020-MSCA-IF-2019 891624, Postdoctoral Fellowship to B.S.), and the University of Manchester (Lectureship to G.J.P.P. and G.E.M.C.).
Publisher Copyright:
© 2021 American Chemical Society.
Keywords:
asymmetric, benzocyclobutenes, copper, indolines, palladium
Identifiers
Local EPrints ID: 478104
URI: http://eprints.soton.ac.uk/id/eprint/478104
ISSN: 2155-5435
PURE UUID: 6796fa04-b17b-405b-a9c7-830c8292ef46
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Date deposited: 21 Jun 2023 16:57
Last modified: 18 Mar 2024 04:11
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Contributors
Author:
Fabien J.T. Talbot
Author:
Shibo Zhang
Author:
Bishnupada Satpathi
Author:
Gareth P. Howell
Author:
Gregory J.P. Perry
Author:
Giacomo E.M. Crisenza
Author:
David J. Procter
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