Evidence map›Paper›PMID 37470111›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Remote C-H Olefination of Heterocyclic Biaryls Enabled by Reversibly Bound Templates.

Luo-Yan Liu, Zhoulong Fan, Md Emdadul Hoque, Shaoqun Qian, Guangrong Meng, Nikita Chekshin, Keita Tanaka, Jennifer X Qiao, Kap-Sun Yeung, Jin-Quan Yu

Abstract read
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In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. 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

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

1 citing paper in PubMed.

  1. 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

10 authors.

Luo-Yan LiuDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Zhoulong FanDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Md Emdadul HoqueDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Shaoqun QianDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Guangrong MengDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Nikita ChekshinDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Keita TanakaDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Jennifer X QiaoDiscovery Chemistry, Bristol-Myers Squibb Company, P.O. Box 4000, Princeton, NJ, 08543, USA.
Kap-Sun YeungDiscovery Chemistry, Bristol-Myers Squibb Research and Development, 100 Binney Street, Cambridge, MA, 02142, USA.
Jin-Quan YuDepartment of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.ORCID http://orcid.org/0000-0003-3560-5774

Funding

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 GM102265NIGMS NIH HHS R01 GM102265 to JQY
6 · The paper itself

Abstract

Remote C-H functionalization of heterocyclic biaryls will be of great importance in synthesis and medicinal chemistry. Through adjusting the geometric relationship of the directing atom and target C-H bonds, two new catalytic templates have been developed to enable the functionalization of the more hindered ortho-C-H bonds of heterobiaryls bearing directing heteroatom at the meta- or para-positions, affording unprecedented site-selectivity. The use of template chaperone also overcomes product inhibition and renders the directing templates catalytic. The utility of this protocol was demonstrated by olefination of heterocyclic biaryls with various substituents, overriding conventional steric and electronic effects. These ortho-C-H olefinated heterobiaryls are sterically hindered and can often be challenging to prepare through aryl-aryl coupling reactions.

Indexed as

C−H ActivationHeterobiarylOlefinationPalladiumSite-Selectivity

Identifiers

PMID37470111
PMCPMC10552871

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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.