Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.

Caleb Karmel, Camille Z Rubel, Elena V Kharitonova, John F Hartwig

Abstract read

In one paragraph

Article in Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

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

The trial behind it

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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.

Sterically Controlled C-H Olefination of Heteroarenes.Angewandte Chemie (International ed. in English) · 2020
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

4 authors.

Caleb KarmelDepartment of Chemistry, University of California, Berkeley, CA, 94720 USA.

Camille Z RubelDepartment of Chemistry, University of California, Berkeley, CA, 94720 USA.

Elena V KharitonovaDepartment of Chemistry, University of California, Berkeley, CA, 94720 USA.

John F HartwigDepartment of Chemistry, University of California, Berkeley, CA, 94720 USA.

Funding

Discovery and Development of Organic Reactions Catalyzed by Transition Metals Valuable for Medicinal ChemistryR35GM130387 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI John F Hartwig · 2019 to 2026

$7.1M

Acquisition of a Cryoprobe and Related Accessories for a 600 MHz NMR Spectrometer to Support Health Research Activities at the University of California, BerkeleyS10OD024998 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI HARTWIG, JOHN F · 2018 to 2018

$265k

NIGMS NIH HHS R35 GM130387NIH HHS S10 OD024998

6 · The paper itself

Abstract

The steric effects of substituents on five-membered rings are less pronounced than those on six-membered rings because of the difference in bond angles. Thus, the regioselectivities of reactions that occur with selectivities dictated by steric effects, such as the borylation of C-H bonds, have been poor in many cases. We report that the silylation of five-membered ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of [Ir(cod)(OMe)]

Indexed as

C-H FunctionalizationHeteroarenesIridium CatalysisSilylation

Identifiers

PMID33071367

DOI10.1002/ange.201916015

PMCPMC7566956

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