Evidence map›Paper›PMID 41217450›Full record

ArticleJournal of the American Chemical Society2025

Electronic Activation Enables the Borylation of Alkyl C-H Bonds in Saturated Nitrogen Heterocycles.

Kyan A D'Angelo, Ruyou Zheng, Isaac F Yu, Melody J Tang, Chris La, Richard T Wetterer, John F Hartwig

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Article
  2. Terminal-Selective spJournal of the American Chemical Society · 2026
    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

7 authors.

Kyan A D'AngeloDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0000-0002-9688-5143
Ruyou ZhengDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0009-0004-1531-7227
Isaac F YuDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0000-0001-9659-2204
Melody J TangDepartment of Chemistry, University of California, Berkeley, California 94720, United States.
Chris LaDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0000-0002-9982-133X
Richard T WettererDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0009-0003-4728-0580
John F HartwigDepartment of Chemistry, University of California, Berkeley, California 94720, United States.ORCID 0000-0002-4157-468X

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
Catalyst- and Reagent-Guided Selective Alkyl C-H Bond FunctionalizationF32GM146425 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI D'ANGELO, KYAN ANTHONY · 2023 to 2025
$174k
NIGMS NIH HHS F32 GM146425NIGMS NIH HHS R35 GM130387NIH HHS S10 OD024998
6 · The paper itself

Abstract

Catalytic functionalization of C-H bonds is a valuable strategy for the synthesis and diversification of organic compounds. The catalytic borylation of heteroaromatic C-H bonds is well established, but the analogous borylation of alkyl C-H bonds in saturated heterocycles remains underdeveloped. Reactions with improved catalysts recently reported for the borylation of alkyl C-H bonds occurred with a narrow range of such nitrogen heterocycles. Here, we describe a broadly applicable approach to activate C-H bonds in saturated nitrogen heterocycles for iridium-catalyzed borylation by installing a group on nitrogen that increases the reactivity of specific C-H bonds. Mechanistic studies reveal that the electron withdrawing groups accelerate the rate of borylation by enhancing the energetics of multiple steps within the catalytic cycle.

Identifiers

PMID41217450
PMCPMC12629849

What OpenQuestion holds

Textmetadata
LicenceTDM
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.