Rh(I)-Catalyzed Cascade Carbonylative Cyclization of Propargyl α-Diazoindolacetates for Construction of Carbazoles

Guo Hao Zhu; Xuefeng Jiang

doi:10.1021/acs.orglett.3c03132

Rh(I)-Catalyzed Cascade Carbonylative Cyclization of Propargyl α-Diazoindolacetates for Construction of Carbazoles

Guo Hao Zhu
, Xuefeng Jiang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

8 Scopus citations

Abstract

A Rh(I)-catalyzed carbene migration/carbonylation/cyclization (MCC) strategy has been established for the construction of diverse functionalized carbazoles from propargyl α-diazoindolacetates. Rh(I)-stabilized carbene with different electrophilic properties displays specific reactivity toward alkyne and CO during the transformation, ensuring the smooth progress of the tandem cyclization. Other heteroaryl scaffolds were achieved simultaneously through this cascade protocol, thus offering a straightforward pathway toward functionalized polycyclic aromatic molecule synthesis.

Original language	English
Pages (from-to)	8077-8082
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	45
DOIs	https://doi.org/10.1021/acs.orglett.3c03132
State	Published - 17 Nov 2023

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title = "Rh(I)-Catalyzed Cascade Carbonylative Cyclization of Propargyl α-Diazoindolacetates for Construction of Carbazoles",

abstract = "A Rh(I)-catalyzed carbene migration/carbonylation/cyclization (MCC) strategy has been established for the construction of diverse functionalized carbazoles from propargyl α-diazoindolacetates. Rh(I)-stabilized carbene with different electrophilic properties displays specific reactivity toward alkyne and CO during the transformation, ensuring the smooth progress of the tandem cyclization. Other heteroaryl scaffolds were achieved simultaneously through this cascade protocol, thus offering a straightforward pathway toward functionalized polycyclic aromatic molecule synthesis.",

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Y1 - 2023/11/17

N2 - A Rh(I)-catalyzed carbene migration/carbonylation/cyclization (MCC) strategy has been established for the construction of diverse functionalized carbazoles from propargyl α-diazoindolacetates. Rh(I)-stabilized carbene with different electrophilic properties displays specific reactivity toward alkyne and CO during the transformation, ensuring the smooth progress of the tandem cyclization. Other heteroaryl scaffolds were achieved simultaneously through this cascade protocol, thus offering a straightforward pathway toward functionalized polycyclic aromatic molecule synthesis.

AB - A Rh(I)-catalyzed carbene migration/carbonylation/cyclization (MCC) strategy has been established for the construction of diverse functionalized carbazoles from propargyl α-diazoindolacetates. Rh(I)-stabilized carbene with different electrophilic properties displays specific reactivity toward alkyne and CO during the transformation, ensuring the smooth progress of the tandem cyclization. Other heteroaryl scaffolds were achieved simultaneously through this cascade protocol, thus offering a straightforward pathway toward functionalized polycyclic aromatic molecule synthesis.

UR - https://www.scopus.com/pages/publications/85178087267

U2 - 10.1021/acs.orglett.3c03132

DO - 10.1021/acs.orglett.3c03132

M3 - 文章

C2 - 37933919

AN - SCOPUS:85178087267

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 45

ER -

Rh(I)-Catalyzed Cascade Carbonylative Cyclization of Propargyl α-Diazoindolacetates for Construction of Carbazoles

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