Lewis Base Catalyzed Synthesis of Sulfur Heterocycles via the C1-Pyridinium Enolate.

Simon Cromwell, Randy Sutio, Changhe Zhang, Georgina K Such, David W Lupton

Abstract read

In one paragraph

Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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0cells of the map it votes in

1citing papers in PubMed

–field-weighted citation impact

1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

Lewis Base Catalyzed Synthesis of Sulfur Heterocycles via the C1-Pyridinium Enolate.Angewandte Chemie (International ed. in English) · 2022
Article

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

5 authors.

Simon CromwellSchool of Chemistry, Monash University, Clayton, 3800, Victoria, Australia.

Randy SutioSchool of Chemistry, Monash University, Clayton, 3800, Victoria, Australia.

Changhe ZhangSchool of Chemistry, University of Melbourne, Parkville, Victoria, Australia.

Georgina K SuchSchool of Chemistry, University of Melbourne, Parkville, Victoria, Australia.ORCID http://orcid.org/0000-0002-2868-5799

David W LuptonSchool of Chemistry, Monash University, Clayton, 3800, Victoria, Australia.ORCID http://orcid.org/0000-0002-0958-4298

Funding

Australian Research Council DP150101522Australian Research Council DP170103567

6 · The paper itself

Abstract

While the addition of C1-Lewis base enolates to carbonyls and related structures are well established, the related addition to thiocarbonyls compounds are unknown. Herein, we report a reaction cascade in which a C1-pyridinium enolate undergos addition to dithioesters, trithiocarbonates and xanthates. The reaction provides access to a range of dihydrothiophenes and dihydrothiopyrans (28-examples). Mechanistic investigations, including isolation of intermediates, electronic correlation, and kinetic isotope effect studies support the viability of an activated acid intermediate giving rise to the C1-pyridinium enolate which undergoes turnover limiting cyclization. Subsequent formation of a β-thiolactone regenerates the catalyst with loss of carbon oxysulfide providing the observed products.

Indexed as

HeterocyclesLewis BaseReaction MechanismsThiocarbonylsThiophenes

Identifiers

PMID35718884

DOI10.1002/anie.202206647

PMCPMC9545057

What OpenQuestion holds

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LicenceCC BY-NC-ND

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.