Organocatalytic Fischer Indolization Using the 2,2′-Biphenol/ B(OH)3 System

Kenji Sugimoto; Yusei Wada; Fumino Kitamura; Yuji Matsuya

doi:10.1055/s-0043-1775363

Organocatalytic Fischer Indolization Using the 2,2′-Biphenol/ B(OH)₃ System

Kenji Sugimoto^*, Yusei Wada, Fumino Kitamura, Yuji Matsuya^*

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

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

Abstract

An organocatalyzed Fischer indolization is established by combining 2,2′-biphenol (10 mol%) and B(OH)₃ (30 mol%) as weak, readily available, and easy-to-handle acids. The inclusion of MgSO₄, which efficiently scavenges NH₃ (a possible acid catalyst poison), appears to be key to the success of this process. The corresponding indoles are obtained in yields of up to 91% using this method.

Original language	English
Pages (from-to)	176-180
Number of pages	5
Journal	Synlett
Volume	36
Issue number	2
DOIs	https://doi.org/10.1055/s-0043-1775363
State	Published - 2024/05/17

Keywords

2,2′-biphenol
Fischer indolization
boric acid
indoles
organocatalyst

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-0043-1775363

Cite this

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title = "Organocatalytic Fischer Indolization Using the 2,2′-Biphenol/ B(OH)3 System",

abstract = "An organocatalyzed Fischer indolization is established by combining 2,2′-biphenol (10 mol%) and B(OH)3 (30 mol%) as weak, readily available, and easy-to-handle acids. The inclusion of MgSO4, which efficiently scavenges NH3 (a possible acid catalyst poison), appears to be key to the success of this process. The corresponding indoles are obtained in yields of up to 91% using this method.",

keywords = "2,2′-biphenol, Fischer indolization, boric acid, indoles, organocatalyst",

author = "Kenji Sugimoto and Yusei Wada and Fumino Kitamura and Yuji Matsuya",

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AU - Sugimoto, Kenji

AU - Wada, Yusei

AU - Kitamura, Fumino

AU - Matsuya, Yuji

PY - 2024/5/17

Y1 - 2024/5/17

N2 - An organocatalyzed Fischer indolization is established by combining 2,2′-biphenol (10 mol%) and B(OH)3 (30 mol%) as weak, readily available, and easy-to-handle acids. The inclusion of MgSO4, which efficiently scavenges NH3 (a possible acid catalyst poison), appears to be key to the success of this process. The corresponding indoles are obtained in yields of up to 91% using this method.

AB - An organocatalyzed Fischer indolization is established by combining 2,2′-biphenol (10 mol%) and B(OH)3 (30 mol%) as weak, readily available, and easy-to-handle acids. The inclusion of MgSO4, which efficiently scavenges NH3 (a possible acid catalyst poison), appears to be key to the success of this process. The corresponding indoles are obtained in yields of up to 91% using this method.

KW - 2,2′-biphenol

KW - Fischer indolization

KW - boric acid

KW - indoles

KW - organocatalyst

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