Evidence map›Paper›PMID 33353940›Full record

ArticleNature communications2020

Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation.

Hui-Qi Ni, Ilia Kevlishvili, Pranali G Bedekar, Joyann S Barber, Shouliang Yang, Michelle Tran-Dubé, Andrew M Romine, Hou-Xiang Lu, Indrawan J McAlpine, Peng Liu and 1 more

Open access · goldAbstract read
In one paragraph

Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.

0numbers the graph read from it
0cells of the map it votes in
20citing papers in PubMed
4.5field-weighted citation impact, top 4% of its field
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

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

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

20 citing papers in PubMed, 62 citations in OpenAlex.

  1. Review
  2. Cobalt-catalyzed alkyne silylamidation unlocksNational science review · 2026
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  6. Reverse Regioselective Dicarbofunctionalization via Anti-Michael-Type Addition.Angewandte Chemie (International ed. in English) · 2025
    Article
  7. Article
  8. Article
  9. Journal of the American Chemical Society · 2024
    Article
  10. Tunable [3+2] and [4+2] annulations for pyrrolidine and piperidine synthesis.Chemical communications (Cambridge, England) · 2023
    Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Pd-Catalyzed Heteroannulation UsingJournal of the American Chemical Society · 2022
    Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. 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

11 authors at 3 institutions in 1 country.

Hui-Qi NiDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Ilia KevlishviliDepartment of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA, 15260, USA.
Pranali G BedekarDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Joyann S BarberPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, CA, 92121, USA.
Shouliang YangPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, CA, 92121, USA.
Michelle Tran-DubéPfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, CA, 92121, USA.
Andrew M RomineDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.ORCID 0000-0002-6703-2926
Hou-Xiang LuDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Indrawan J McAlpinePfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, CA, 92121, USA. indrawan.mcalpine@pfizer.com.ORCID 0000-0002-4230-4892
Peng LiuDepartment of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA, 15260, USA. pengliu@pitt.edu.ORCID 0000-0002-8188-632X
Keary M EngleDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA. keary@scripps.edu.ORCID 0000-0003-2767-6556
Scripps Research Institute · USPfizer (United States) · USUniversity of Pittsburgh · US

Funding

Combinatorial, Catalytic Functionalization of Alkenes and AlkynesR35GM125052 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI ENGLE, KEARY MARK · 2017 to 2021
$2.9M
Computational Models for Reactivity and Selectivity in Transition Metal-Catalyzed Olefin FunctionalizationR35GM128779 · NIGMS · UNIVERSITY OF PITTSBURGH AT PITTSBURGH · PI Peng Liu · 2018 to 2026
$2.9M
NIGMS NIH HHS R35 GM125052NIGMS NIH HHS R35 GM128779
6 · The paper itself

Abstract

2,3-Dihydrobenzofurans and indolines are common substructures in medicines and natural products. Herein, we describe a method that enables direct access to these core structures from non-conjugated alkenyl amides and ortho-iodoanilines/phenols. Under palladium(II) catalysis this [3 + 2] heteroannulation proceeds in an anti-selective fashion and tolerates a wide variety of functional groups. N-Acetyl, -tosyl, and -alkyl substituted ortho-iodoanilines, as well as free -NH

Indexed as

AlkenesAniline CompoundsComputer SimulationPalladiumPhenolsThermodynamicsAlkenesanilineAniline CompoundsPalladiumPhenols

Identifiers

PMID33353940
PMCPMC7755910
OpenAlexW3115237719

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

Registered trials

None linked

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.