Fischer indole synthesis with organozinc reagents

Benjamin A. Haag; Zhi Guang Zhang; Jin Shan Li; Paul Knochel

doi:10.1002/anie.201005319

Fischer indole synthesis with organozinc reagents

Benjamin A. Haag
, Zhi Guang Zhang
, Jin Shan Li
, Paul Knochel

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

86 Scopus citations

Abstract

Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]-sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity.

Original language	English
Pages (from-to)	9513-9516
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	49
DOIs	https://doi.org/10.1002/anie.201005319
State	Published - 3 Dec 2010
Externally published	Yes

Keywords

annulation
diazo compounds
indoles
nitrogen heterocycles
zinc

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10.1002/anie.201005319

Cite this

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abstract = "Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]-sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity.",

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T1 - Fischer indole synthesis with organozinc reagents

AU - Haag, Benjamin A.

AU - Zhang, Zhi Guang

AU - Li, Jin Shan

AU - Knochel, Paul

PY - 2010/12/3

Y1 - 2010/12/3

N2 - Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]-sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity.

AB - Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]-sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity.

KW - annulation

KW - diazo compounds

KW - indoles

KW - nitrogen heterocycles

KW - zinc

UR - https://www.scopus.com/pages/publications/78650127892

U2 - 10.1002/anie.201005319

DO - 10.1002/anie.201005319

M3 - 文章

C2 - 20979062

AN - SCOPUS:78650127892

SN - 1433-7851

VL - 49

SP - 9513

EP - 9516

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 49

ER -

Fischer indole synthesis with organozinc reagents

Abstract

Keywords

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