Synthesis 2023; 55(12): 1922-1928
DOI: 10.1055/a-2039-6271
paper
Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry

Synthesis of 1,1-Disubstituted Indenes via Palladium-Catalyzed Cross-Coupling of ortho-Alkenyl Bromobenzenes and α-Aryl-α-diazoesters

Xiao-Jiao Feng
,
Jian-Guo Fu
,
Qian Zhao
,
Yu-Han Lu
,
Shu-Sheng Zhang∗
,
Chen-Guo Feng∗
This work was supported by the National Natural Science Foundation of China (22271195), the Science and Technology Commission of Shanghai Municipality (21ZR1482100 and 22ZR1458900), the Shanghai Municipal Education Commission (2019-01-07-00-10-E00072), Shanghai Science and Technology Development Fund from Central Leading Local Government (YDZX20223100001004), and Shanghai Municipal Health Commission/Shanghai Municipal Administration of Traditional Chinese Medicine (ZY(2021–2023)-0501).
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Dedication to Professor Guo-Qiang Lin on the Occasion of his 80th Birthday

Abstract

Palladium-catalyzed cross-coupling of ortho-alkenyl bromobenzenes and α-aryl-α-diazoesters was realized. The reactions proceeded in moderate to excellent yields with broad substrate scope, providing a straightforward method for the synthesis of 1,1-disubstituted indenes. The reaction is thought to undergo a tandem alkenyl C–H activation/carbene insertion sequence, in which a C,C-pallada(II)cycle is the key intermediate.

Key words

palladium catalyst - alkenyl C–H activation - carbene insertion - indene

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2039-6271.
  • Supporting Information


Publication History

Received: 20 January 2023

Accepted after revision: 21 February 2023

Accepted Manuscript online:
21 February 2023

Article published online:
29 March 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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