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Pd‐PEPPSI‐IPent: An Active, Sterically Demanding Cross‐Coupling Catalyst and Its Application in the Synthesis of Tetra‐<i>Ortho</i>‐Substituted Biaryls

2009· article· en· 393 citations· W2152876843 on OpenAlex· 10.1002/anie.200805661

Why is this work in the frame?

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

Canadian affiliationAn author listed a Canadian institution. This is the only route the usual frame has.

The three-model screen

all 1,000 screened works →

All three models called this out of scope.

stratum: aff_core · design weight: 5595.24 (the sample is stratified; any rate computed without the weight is wrong)
Claude Opus 4.8OUT
genre: empirical
about Canada: no
confidence: high

Development of a cross-coupling catalyst; synthetic chemistry.

GPT-5.6 (high)OUT
genre: empirical
about Canada: no
confidence: high

This evaluates chemical catalysts for a cross-coupling reaction, not research itself.

Grok 4.5OUT
genre: empirical
about Canada: no
confidence: high

Synthetic organometallic catalysis for biaryl cross-coupling; domain chemistry.

Abstract

Incredible Bulk: A series of N-heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki-Miyaura reaction. A variety of sterically encumbered tetra-ortho-substituted biaryl products were formed from unreactive aryl chlorides using the isopentyl-substituted catalyst at temperatures ranging from 65 degrees C to room temperature. The cyclopentyl-substituted catalyst was virtually inactive, demonstrating that "flexible bulk" is essential to promote these transformations.

Stored with the screening record, where it is evidence for the labels above.

The record

Venue
Angewandte Chemie International Edition
Topic
Catalytic Cross-Coupling Reactions
Field
Chemistry
Canadian institutions
University of TorontoYork University
Funders
Keywords
Steric effectsCarbeneCatalysisTetraArylChemistryCoupling reactionPolymer chemistryOrganic chemistryCombinatorial chemistryMedicinal chemistry
Has abstract in OpenAlex
yes