Stereoselective vicinal C(sp³)-C bond formation via metallaphotoredox 1,2-difunctionalization of internal alkenes.

Yanyan Zhang, Tianyu Long, Yangxing Sun, Ye Yuan, Jing Li, Chuqian Tang, Feng-Ling Qing, Lingling Chu

Abstract read

In one paragraph

Article in Nature communications, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it

0cells of the map it votes in

0citing 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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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.

Yanyan Zhang *State Key Laboratory of Advanced Fiber Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, China.

Tianyu Long *State Key Laboratory of Advanced Fiber Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, China.

Yangxing Sun *State Key Laboratory of Advanced Fiber Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, China.

Ye YuanState Key Laboratory of Advanced Fiber Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, China.

Jing LiState Key Laboratory of Advanced Fiber Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, China.

Chuqian TangState Key Laboratory of Advanced Fiber Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, China.

Feng-Ling QingKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China. flq@mail.sioc.ac.cn.

Lingling ChuState Key Laboratory of Advanced Fiber Materials, College of Chemistry and Chemical Engineering, Center for Advanced Low-Dimension Materials, Donghua University, Shanghai, China. lingling.chu1@dhu.edu.cn.ORCID http://orcid.org/0000-0001-7969-0531

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Achieving precise stereocontrol when forging two vicinal C(sp³)-C bonds on unsymmetrical internal alkenes remains a formidable challenge. The comparable reactivity of alkyl radicals often compromises chemo- and regioselectivity, while the concurrent induction of diastereo- and enantioselectivity has proven elusive. Here, we show a unified metallaphotoredox strategy that addresses these challenges through two complementary multicomponent difunctionalization protocols. First, a Ni/terpyridine catalyst system enables anti-selective 1,2-dialkylation of both cyclic and acyclic internal alkenes, delivering vicinal C(sp³)-C(sp³) linkages with high levels of chemo-, regio-, and diastereoselectivity. A switch to a chiral biimidazole ligand and replacement of the alkyl halide with a (hetero)aryl bromide unlocks enantioselective 1,2-alkylarylation of cyclic internal alkenes. This transformation affords β-aryl-α-alkylated lactones and related scaffolds bearing two contiguous stereocenters with excellent diastereo- and enantioselective control. This dual strategy offers a rapid and efficient access to drug-like molecular architectures.

Identifiers

PMID41730869

DOI10.1038/s41467-026-69838-7

PMCPMC13039993

What Socratic holds

Textmetadata

LicenceCC BY-NC-ND

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 Socratic graph.