Phosphine-Mediated Sequential [2+4]/[2+3] Annulation to Construct Pyrroloquinolines.

Org Lett

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

Published: March 2022

A domino [2+4]/[2+3] sequential annulation reaction of MBH carbonates with N-unprotected indoles has been developed to provide various pyrroloquinoline derivatives in ≤94% yield and 20:1 dr. The reaction could be either mediated by stoichiometric PCy or catalyzed by RPO via P/P═O redox cycling in the presence of phenylsilane. This method assembles polycyclic 1,7-fused indoles in one step diastereoselectively.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.1c04388DOI Listing

Publication Analysis

Top Keywords

phosphine-mediated sequential
4
sequential [2+4]/[2+3]
4
[2+4]/[2+3] annulation
4
annulation construct
4
construct pyrroloquinolines
4
pyrroloquinolines domino
4
domino [2+4]/[2+3]
4
[2+4]/[2+3] sequential
4
sequential annulation
4
annulation reaction
4

Similar Publications

Stable and easy-to-handle sodium salts of sulfonyl oximes were first identified to proceed via visible-light-driven phophine-mediated successive deoxygenation to realize the -Markovnikov hydrothiolation of alkenes, which could serve as an odorless sulfur source. Mechanistic studies revealed that the key thiyl radical intermediate could be generated from the sulfonyl oxime anion via a phosphine-mediated fragmentation and a sequential deoxygenation process. Notably, a wide range of alkenes, including acrylamides, acrylates, vinyl ketones, vinyl sulfones, and acrylonitriles, are competent substrates for this protocol, which is highly beneficial for the construction of structurally diversified organosulfur compounds.

View Article and Find Full Text PDF

The chemical activation of water would allow this earth-abundant resource to be transferred into value-added compounds, and is a topic of keen interest in energy research. Here, we demonstrate water activation with a photocatalytic phosphine-mediated radical process under mild conditions. This reaction generates a metal-free PR-HO radical cation intermediate, in which both hydrogen atoms are used in the subsequent chemical transformation through sequential heterolytic (H) and homolytic (H) cleavage of the two O-H bonds.

View Article and Find Full Text PDF

Phosphine-Mediated Sequential [2+4]/[2+3] Annulation to Construct Pyrroloquinolines.

Org Lett

March 2022

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

A domino [2+4]/[2+3] sequential annulation reaction of MBH carbonates with N-unprotected indoles has been developed to provide various pyrroloquinoline derivatives in ≤94% yield and 20:1 dr. The reaction could be either mediated by stoichiometric PCy or catalyzed by RPO via P/P═O redox cycling in the presence of phenylsilane. This method assembles polycyclic 1,7-fused indoles in one step diastereoselectively.

View Article and Find Full Text PDF

Phosphine-mediated sequential annulations of allenyl ketone and isocyanide: a bicyclization strategy to access a furan-fused eight-membered ring and a spirocycle.

Chem Commun (Camb)

October 2019

Department of Chemistry, Center for Supramolecular Chemistry and Catalysis, College of Sciences & Institute for Sustainable Energy, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. China.

Phosphine-mediated cascade annulations of allenyl ketone and isocyanide have been disclosed. Two molecular allenyl ketones work as different four-carbon synthons to form two rings, respectively, and thus enables the efficient synthesis of a furan-fused eight-membered ring and a spirocycle.

View Article and Find Full Text PDF

Phosphine-Mediated Sequential Annulation Reaction: Access to Functionalized Benzofurans and 4,5-Dihydrobenzofurans.

Chemistry

June 2017

State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, P.R. China.

A new strategy for the facile access to multi-functionalized benzofurans and 4,5-dihydrobenzofurans has been explored. The advantages of the present protocol include readily obtainable starting materials, mild and metal-free conditions, expedient and practical processes, excellent yields, and easy scale-up. The reaction demonstrated high efficiency to construct two rings in a single step.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!