Fischer Indole Synthesis with Organozinc Reagents

Haag, Benjamin A.; Zhang, Zhiguang; Li, Jinshan; Knöchel, Paul

doi:10.1002/anie.201005319

Cited by 82 publications

(28 citation statements)

References 65 publications

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“…[4] Historically, the most common method is the Fischer indole synthesis, but this reaction can be limited in scope due to the stability of the hydrazine component, preparation of aryl hydrazines, and strong acidic conditions. [3,5] The Bischler-Möhlau synthesis of 2-aryl indoles usually requires high temperatures that can lead to low yields and regiochemistry problems. [6] To enable new strategies to access this key heterocycle, modern chemical research has focused on transition metal-catalyzed approaches (Scheme 1).…”

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confidence: 99%

N‐Heterocyclic‐Carbene‐Catalyzed Synthesis of 2‐Aryl Indoles

et al. 2014

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A convergent and efficient transition‐metal‐free catalytic synthesis of 2‐aryl‐indoles has been developed. The interception of a highly reactive and transient aza‐ortho‐quinone methide by an acyl anion equivalent generated through N‐hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.

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confidence: 99%

N‐Heterocyclic‐Carbene‐Catalyzed Synthesis of 2‐Aryl Indoles

et al. 2014

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“…[1] Consequently, numerous efforts have been devoted to the development of efficient methods to construct the indole architecture. Despite its extensive applications [4] and various improvements, [5] the Fischer indole synthesis has several limitations, including poor regioselectivity with nonsymmetric ketones, a restricted range of starting materials, and harsh reaction conditions such as the use of strong acids and/or elevated temperatures. Despite its extensive applications [4] and various improvements, [5] the Fischer indole synthesis has several limitations, including poor regioselectivity with nonsymmetric ketones, a restricted range of starting materials, and harsh reaction conditions such as the use of strong acids and/or elevated temperatures.…”

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confidence: 99%

Synthesis of Indoles through Highly Efficient Cascade Reactions of Sulfur Ylides and N‐(ortho‐Chloromethyl)aryl Amides

et al. 2012

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“…and various improvements, [5] the Fischer indole synthesis has several limitations, including poor regioselectivity with nonsymmetric ketones, a restricted range of starting materials, and harsh reaction conditions such as the use of strong acids and/or elevated temperatures. [2] As a consequence, the demand for alternative efficient methods has encouraged the development of new methods for the synthesis of indoles.…”

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confidence: 99%