Issue 14, 2023
From the journal:

Organic Chemistry Frontiers

Palladium-catalyzed cascade cyclization/intramolecular redox-relay Heck arylation of alkenols: access to tetrahydro-β-carbolines from 2-(hydroxyalkenynyl)sulfonanilides†

Tao Liu,a   Tuanli Yao, ORCID logo *a   Ruihua Guo*bc  and  Xiangyang Qin*d  

* Corresponding authors

a Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an, China
E-mail: yaotuanli@sust.edu.cn

b College of Food Science and Technology, Shanghai Ocean University, Shanghai, China

c Marine Biomedical Science and Technology Innovation Platform of Lin-gang Special Area, Shanghai, China

d Department of Chemistry, School of Pharmacy, Air Force Medical University, Xi'an, China

Abstract

A palladium-catalyzed cascade reaction for the synthesis of tetrahydro-β-carbolines and other polycyclic indoles from 2-(hydroxyenyl)sulfonanilides by combining the Pd(II)-catalyzed cyclization of alkynes and intramolecular redox-relay Heck arylation of alkenols is presented. This method enables the construction of two rings and installs a remote carbonyl group in a single operation, offering broad synthetic utility for further elaborations.

Graphical abstract: Palladium-catalyzed cascade cyclization/intramolecular redox-relay Heck arylation of alkenols: access to tetrahydro-β-carbolines from 2-(hydroxyalkenynyl)sulfonanilides

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Article information

DOI
https://doi.org/10.1039/D3QO00620D
Article type
Research Article
Submitted
26 Apr 2023
Accepted
30 May 2023
First published
30 May 2023

Org. Chem. Front., 2023,10, 3504-3508

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Palladium-catalyzed cascade cyclization/intramolecular redox-relay Heck arylation of alkenols: access to tetrahydro-β-carbolines from 2-(hydroxyalkenynyl)sulfonanilides

T. Liu, T. Yao, R. Guo and X. Qin, Org. Chem. Front., 2023, 10, 3504 DOI: 10.1039/D3QO00620D

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