Synthesis of 2-BMIDA indoles via heteroannulation: applications in drug scaffold and natural product synthesis

George Bell; James W. B. Fyfe; Eva M. Israel; Alexandra M. Z. Slawin; Matthew Campbell; Allan J. B. Watson

doi:10.1021/acs.orglett.2c00959

Synthesis of 2-BMIDA indoles via heteroannulation: applications in drug scaffold and natural product synthesis

George Bell, James W. B. Fyfe, Eva M. Israel, Alexandra M. Z. Slawin, Matthew Campbell, Allan J. B. Watson^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

A Pd-catalyzed heteroannulation approach for the synthesis of C2 borylated indoles is reported. The process allows access to highly functionalized 2-borylated indole scaffolds with complete control of regioselectivity. The utility of the process is demonstrated in the synthesis of borylated sulfa drugs and in the concise synthesis of the Aspidosperma alkaloid Goniomitine.

Original language	English
Number of pages	4
Journal	Organic Letters
Volume	Articles ASAP
Early online date	15 Apr 2022
DOIs	https://doi.org/10.1021/acs.orglett.2c00959
Publication status	E-pub ahead of print - 15 Apr 2022

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10.1021/acs.orglett.2c00959Licence: CC BY

Bell_2022_OL_2-BMIDAindoles_CC
© 2022 The Authors. Published by American Chemical Society. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 953 KBLicence: CC BY

CCDC 2149746 & 2133112: Experimental Crystal Structure Determination
Bell, G. E. (Creator), Fyfe, J. W. B. (Creator), Israel, E. M. (Creator), Slawin, A. M. Z. (Creator), Campbell, M. (Creator) & Watson, A. J. B. (Creator), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc2b4zn4, https://dx.doi.org/10.5517/ccdc.csd.cc29lp2p
Dataset
Synthesis of 2-BMIDA indoles via heteroannulation: Applications in drug scaffold and natural product synthesis (dataset)
Bell, G. (Creator), Fyfe, J. (Creator), Israel, E. M. (Creator), Slawin, A. M. Z. (Creator), Campbell, M. (Creator) & Watson, A. J. B. (Creator), University of St Andrews, 15 Apr 2022
DOI: 10.17630/0b2039ef-8b9f-47a1-af8a-3d6c93eb95af
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Cite this

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title = "Synthesis of 2-BMIDA indoles via heteroannulation: applications in drug scaffold and natural product synthesis",

abstract = "A Pd-catalyzed heteroannulation approach for the synthesis of C2 borylated indoles is reported. The process allows access to highly functionalized 2-borylated indole scaffolds with complete control of regioselectivity. The utility of the process is demonstrated in the synthesis of borylated sulfa drugs and in the concise synthesis of the Aspidosperma alkaloid Goniomitine.",

author = "George Bell and Fyfe, {James W. B.} and Israel, {Eva M.} and Slawin, {Alexandra M. Z.} and Matthew Campbell and Watson, {Allan J. B.}",

note = "G.E.B. thanks the EPSRC and GSK for a PhD studentship. J.W.B.F. thanks the Leverhulme Trust for postdoctoral funding (RPG-2018-362). ",

year = "2022",

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day = "15",

doi = "10.1021/acs.orglett.2c00959",

language = "English",

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TY - JOUR

T1 - Synthesis of 2-BMIDA indoles via heteroannulation

T2 - applications in drug scaffold and natural product synthesis

AU - Bell, George

AU - Fyfe, James W. B.

AU - Israel, Eva M.

AU - Slawin, Alexandra M. Z.

AU - Campbell, Matthew

AU - Watson, Allan J. B.

N1 - G.E.B. thanks the EPSRC and GSK for a PhD studentship. J.W.B.F. thanks the Leverhulme Trust for postdoctoral funding (RPG-2018-362).

PY - 2022/4/15

Y1 - 2022/4/15

N2 - A Pd-catalyzed heteroannulation approach for the synthesis of C2 borylated indoles is reported. The process allows access to highly functionalized 2-borylated indole scaffolds with complete control of regioselectivity. The utility of the process is demonstrated in the synthesis of borylated sulfa drugs and in the concise synthesis of the Aspidosperma alkaloid Goniomitine.

AB - A Pd-catalyzed heteroannulation approach for the synthesis of C2 borylated indoles is reported. The process allows access to highly functionalized 2-borylated indole scaffolds with complete control of regioselectivity. The utility of the process is demonstrated in the synthesis of borylated sulfa drugs and in the concise synthesis of the Aspidosperma alkaloid Goniomitine.

U2 - 10.1021/acs.orglett.2c00959

DO - 10.1021/acs.orglett.2c00959

M3 - Article

SN - 1523-7060

VL - Articles ASAP

JO - Organic Letters

JF - Organic Letters

ER -

Synthesis of 2-BMIDA indoles via heteroannulation: applications in drug scaffold and natural product synthesis

Abstract

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Datasets

CCDC 2149746 & 2133112: Experimental Crystal Structure Determination

Synthesis of 2-BMIDA indoles via heteroannulation: Applications in drug scaffold and natural product synthesis (dataset)

Cite this