Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines

Jordy M. Saya, Ellen D.H. van Wordragen, Romano V.A. Orru, Eelco Ruijter

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.

Original languageEnglish
Pages (from-to)1-6
Number of pages6
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusE-pub ahead of print - 3 Jan 2019

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Allylation
indoles
Indoles
products
Biological Products
Derivatives
synthesis
indole

Keywords

  • Allylation
  • Boron reagents
  • Heterocycles
  • Indoles
  • Synthetic methods

Cite this

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title = "Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines",
abstract = "C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.",
keywords = "Allylation, Boron reagents, Heterocycles, Indoles, Synthetic methods",
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Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines. / Saya, Jordy M.; van Wordragen, Ellen D.H.; Orru, Romano V.A.; Ruijter, Eelco.

In: European Journal of Organic Chemistry, 03.01.2019, p. 1-6.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines

AU - Saya, Jordy M.

AU - van Wordragen, Ellen D.H.

AU - Orru, Romano V.A.

AU - Ruijter, Eelco

PY - 2019/1/3

Y1 - 2019/1/3

N2 - C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.

AB - C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.

KW - Allylation

KW - Boron reagents

KW - Heterocycles

KW - Indoles

KW - Synthetic methods

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