Student or educator? Sign up with your school email and get 6 months of Pro free.
CoChat
Sign Up
Cited by 445

The DOI matches its Crossref record; 53 of the 53 references it cites were found in a registry or an index.

Photoactive Chiral Metal–Organic Frameworks for Light-Driven Asymmetric α-Alkylation of Aldehydes

Wu, Pengyan, He, Cheng, Wang, Jian, Peng, Xiaojun, Li, Xuezhao, An, Yonglin, Duan, Chunying·2012·Journal of the American Chemical Society
DOI 10.1021/ja305367j
Open this paper in CoChat — free account

Abstract

Chiral metal-organic frameworks (MOFs) with porous and tunable nature show promise as heterogeneous asymmetric catalysts. Through incorporating the stereoselective organocatalyst L- or D-pyrrolidin-2-ylimidazole (PYI) and a triphenylamine photoredox group into a single framework, we have developed two enantiomeric MOFs, Zn-PYI1 and Zn-PYI2, to prompt the asymmetric α-alkylation of aliphatic aldehydes in a heterogeneous manner. The strong reductive excited state of the triphenylamaine moiety within these MOFs initiated a photoinduced electron transfer, rendering an active intermediate for the α-alkylation. The chiral PYI moieties acted as cooperative organocatalytic active sites to drive the asymmetric catalysis with significant stereoselectivity. Control experiments using the lanthanide-based metal-organic frameworks Ho-TCA and MOF-150, assembled from 4,4',4"-nitrilotribenzoic acid, as catalysts suggested that both the photosensitizer triphenylamine moiety and the chiral organocatalyst D-/L-PYI moiety were necessary for the light-driven α-alkylation reactions. Further investigations demonstrated that the integration of both photocatalyst and asymmetric organocatalyst into a single MOF makes the enantioselection superior to that of simply mixing the corresponding MOFs with the chiral adduct. The easy availability, excellent stereoselectivity, great separability, and individual components fixed with their well-defined porous and repeating structures make the MOF a versatile platform for a new type of tandem catalyst and cooperative catalyst.

Overview

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1021/ja305367j

Cites

53 of 53 references verified0 citation errors · 0 not checkable

Statistics

Verification

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Citations

Cites

Cited by

See all 445

Metadata

Authors
Wu, P., He, C., Wang, J., Peng, X., Li, X., An, Y., & Duan, C.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2012-08-31
Volume
134
Issue
36
Pages
14991-14999
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja305367j
OpenAlex
W2316479035
Cited by
445
References
53
FWCI
25.52
Type
journal article
Language
en
Open access
closed

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Data sources

Bibliographic data: Semantic Scholar, OpenAlex, Crossref.

Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.