Evidence map›Paper›PMID 26226056›Full record

ArticleThe Journal of organic chemistry2015

Harnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization.

Venkata A Kallepalli, Kristin A Gore, Feng Shi, Luis Sanchez, Ghayoor A Chotana, Susanne L Miller, Robert E Maleczka, Milton R Smith

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.

0numbers the graph read from it
0cells of the map it votes in
21citing 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

21 citing papers in PubMed.

  1. Article
  2. Deuteration of Six-Membered N-Heteroarenes: Chemistry and Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Review
  3. Article
  4. Article
  5. Article
  6. Article
  7. Access to C(spRSC advances · 2024
    Article
  8. Review
  9. Article
  10. Article
  11. Palladium-Catalyzed Nondirected Late-Stage C-H Deuteration of Arenes.Journal of the American Chemical Society · 2021
    Article
  12. Review
  13. Article
  14. Article
  15. Article
  16. Indolylboronic Acids: Preparation and Applications.Molecules (Basel, Switzerland) · 2019
    Review
  17. Article
  18. Article
  19. Synthesis of 2-D-Tetrahedron · 2019
    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.

Venkata A KallepalliDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Kristin A GoreDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Feng ShiDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Luis SanchezDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Ghayoor A ChotanaDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Susanne L MillerDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Robert E MaleczkaDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
Milton R SmithDepartment of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.

Funding

Metal-Catalyzed C-H Borylation: Mechanism, Scope, and ApplicationsR01GM063188 · NIGMS · MICHIGAN STATE UNIVERSITY · PI SMITH, MILTON RUDOLPH · 2001 to 2020
$3.4M
Metal-Catalyzed C-H Borylation: Mechanism, Scope, and ApplicationsR56GM063188 · NIGMS · MICHIGAN STATE UNIVERSITY · PI SMITH, MILTON R · 2007 to 2007
$236k
NIGMS NIH HHS GM63188NIGMS NIH HHS R01 GM063188NIGMS NIH HHS R56 GM063188
6 · The paper itself

Abstract

Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as clopidogrel.

Indexed as

Boron CompoundsBoronic AcidsCatalysisDeuteriumEstersIndolesMolecular StructureBoron CompoundsBoronic AcidsDeuteriumEstersIndoles

Identifiers

PMID26226056
PMCPMC5080619

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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.