Evidence map›Paper›PMID 38419352›Full record

ReviewAngewandte Chemie (International ed. in English)2024

Palladium (II)-Catalyzed C-H Activation with Bifunctional Ligands: From Curiosity to Industrialization.

Kevin Wu, Nelson Lam, Daniel A Strassfeld, Zhoulong Fan, Jennifer X Qiao, Tao Liu, Dean Stamos, Jin-Quan Yu

Abstract readReview
In one paragraph

Review in Angewandte Chemie (International ed. in English), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.

0numbers the graph read from it
0cells of the map it votes in
24citing 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

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

24 citing papers in PubMed.

  1. Alkyl-to-Alkyl Palladium Migration Enables Remote C-C Bond Formation.Journal of the American Chemical Society · 2026
    Article
  2. Chiral Spiro-Scaffolded C(spAngewandte Chemie (International ed. in English) · 2026
    Article
  3. Ligand-Enabled Stereoselective Coupling of Methylene C(spAngewandte Chemie (International ed. in English) · 2026
    Article
  4. Review
  5. Article
  6. Review
  7. Article
  8. Conformation-driven C3-C(Nature catalysis · 2026
    Article
  9. Article
  10. Elucidating Ligand-Dependent Selectivities in Pd-Catalyzed C-H Activations.Angewandte Chemie (International ed. in English) · 2025
    Article
  11. Review
  12. Ligand-Controlled Alkylation-Heck-C(spJournal of the American Chemical Society · 2025
    Article
  13. Article
  14. Article
  15. Article
  16. COAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
    Article
  17. Article
  18. Enantioselective β-C(spJournal of the American Chemical Society · 2025
    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

8 authors.

Kevin WuDepartment of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Nelson LamDepartment of Chemistry, Cambridge University, Cambridge, CB2 1EW, UK.
Daniel A StrassfeldDepartment of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Zhoulong FanDepartment of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Jennifer X QiaoSmall Molecule Drug Discovery, Bristol-Myers Squibb Research and Development, 250 Water Street, Cambridge, MA 02141, USA.
Tao LiuDiscovery Chemistry Research & Technology Eli Lilly and Company, Lilly Biotechnology Center, 10290 Campus Point Dr, San Diego, CA 92121, USA.
Dean StamosResearch & Development, Flagship Pioneering, 55 Cambridge Parkway Suite 800E, Cambridge, MA 02142, USA.
Jin-Quan YuDepartment of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.ORCID https://orcid.org/0000-0003-3560-5774

Funding

Ligand-promoted Enantioselective C-H Activation ReactionsR01GM084019 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI YU, JIN-QUAN · 2008 to 2024
$9.5M
Catalyst-Controlled Site-Selective C-H Functionalizations of Arenes and HeteroarenesR01GM102265 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI YU, JIN-QUAN · 2012 to 2023
$4.6M
NIGMS NIH HHS R01 GM084019NIGMS NIH HHS R01 GM102265NIH HHS R01 GM084019NIH HHS R01 GM102265
6 · The paper itself

Abstract

In 2001, our curiosity to understand the stereochemistry of C-H metalation with Pd prompted our first studies in Pd(II)-catalyzed asymmetric C-H activation (RSC Research appointment: 020 7451 2545, Grant: RG 36873, Dec. 2002). We identified four central challenges: 1. poor reactivity of simple Pd salts with native substrates; 2. few strategies to control site selectivity for remote C-H bonds; 3. the lack of chiral catalysts to achieve enantioselectivity via asymmetric C-H metalation, and 4. low practicality due to limited coupling partner scope and the use of specialized oxidants. These challenges necessitated new strategies in catalyst and reaction development. For reactivity, we developed approaches to enhance substrate-catalyst affinity together with novel bifunctional ligands which participate in and accelerate the C-H cleavage step. For site-selectivity, we introduced the concept of systematically modulating the distance and geometry between a directing template, catalyst, and substrate to selectively access remote C-H bonds. For enantioselectivity, we devised predictable stereomodels for catalyst-controlled enantioselective C-H activation based on the participation of bifunctional ligands. Finally, for practicality, we have developed varied catalytic manifolds for Pd(II) to accommodate diverse coupling partners while employing practical oxidants such as simple peroxides. These advances have culminated in numerous C-H activation reactions, setting the stage for broad industrial applications.

Indexed as

catalysisC−H activationC−H functionalizationligand developmenttransition metal

Identifiers

PMID38419352
PMCPMC11216193

What OpenQuestion holds

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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.