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Synlett 2021; 32(01): 69-74
DOI: 10.1055/s-0040-1707192
letter
© Georg Thieme Verlag Stuttgart · New York

Cascade Access to Carboline Carboxylates from Indolyl Ketoximes and Acrylates via Palladium-Catalyzed C–H Bond Alkenylation/Annulation

Xiao-Pan Fu
a   Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Email: jyf@ecust.edu.cn
,
Lu Chen
a   Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Email: jyf@ecust.edu.cn
,
Gao-Rong Wu
a   Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Email: jyf@ecust.edu.cn
,
Hong-Wei Liu
a   Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Email: jyf@ecust.edu.cn
,
Cheng-Cai Xia∗
b   Pharmacy College, Shandong First Medical University and Shandong Academy of Medical Sciences, 619 Changcheng Road, Taian 271016, P. R. of China   Email: xiachc@163.com
,
Ya-Fei Ji∗
a   Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China   Email: jyf@ecust.edu.cn
› Author AffiliationsWe gratefully thank the National Natural Science Foundation of China (Project No. 21676088) for financial support.
Further Information

Publication History

Received: 13 May 2020

Accepted after revision: 11 June 2020

Publication Date:
15 July 2020 (online)

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Abstract

An efficient palladium-catalyzed C–H bond alkenylation/annulation strategy to access carboline carboxylates from indolyl ketoximes and acrylates through C–C/C–N bond formation is reported. Indolyl ketoximes not only direct ortho-olefination with acrylates, but also undergo an intramolecular N–O bond cleavage/traceless annulation to construct carboline carboxylates straightforwardly in this concise method.

Key words

carboline carboxylates - alkenylation - annulation - indolyl ketoximes - C–H activation - palladium catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707192.
  • Supporting Information
 

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