Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones.

Amy Boylan, Thien S Nguyen, Brian J Lundy, Jian-Yuan Li, Ravikrishna Vallakati, Sasha Sundstrom, Jeremy A May

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2021. 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.

Chiral binaphthol-catalyzed enantioselective conjugate addition of alkenyl trifluoroborate salts to alkenyl-substituted benzothiazoles.RSC advances · 2025
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.

Amy BoylanDepartment of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.ORCID 0000-0002-2317-3196

Thien S NguyenDepartment of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.

Brian J LundyDepartment of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.

Jian-Yuan LiDepartment of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.

Ravikrishna VallakatiDepartment of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.

Sasha SundstromDepartment of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.

Jeremy A MayDepartment of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, TX 77204-5003, USA.ORCID 0000-0003-3319-0077

Funding

National Science Foundation CHE-1352439Welch Foundation E-1744

6 · The paper itself

Abstract

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

Indexed as

enantioselective conjugate additionheterocyclesindolepyrrole

Identifiers

PMID33799473

DOI10.3390/molecules26061615

PMCPMC8000498

What OpenQuestion holds

Textmetadata

LicenceCC BY

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.