Skip to content
DraconiticResearch
Search Sources API
203,203 studies31 sourcesUpdated 24 min ago
Peer-reviewedCC BYJournal of the American Chemical Society

Regioselective and Stereodivergent C-H Functionalization of Internal Alkenes.

  • Elizabeth A Ryutov1
  • Peter J Verardi1
  • Song N Dang1
  • Karina Targos1
  • Leah C Garman1
  • Zachary K Wickens1
  1. 1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin53706, United States.
Read full textPDFDOICite

Abstract

Herein, we introduce a new strategy for the regioselective and stereodivergent C-H functionalization of internal alkenes. We discovered that the regioselectivity of internal alkene thianthrenation is exceptionally electronically sensitive and can be controlled by native allylic and homoallylic functional groups. We also found that both alkenyl thianthrenium stereoisomers can be selectively accessed by using different workup conditions. While thianthrenation is typically stereoretentive, the addition of Cs2CO3 in the workup induces isomerization through reversible conjugate addition. We show that both stereoisomers of the alkenyl linchpins can be readily engaged in stereoretentive cross coupling reactions. This selective thianthrenation-coupling sequence introduces a generalizable platform for stereodefined trisubstituted alkene synthesis.

Related

  1. Supramolecular Mask-Mediated Regioselective bis-Bingel-Functionalization of M3N@Ih-C80 (M = Lu, Sc).
    Valentina Iannace, Clara Sabrià, Sheng Zhu +10
    Journal of the American Chemical SocietyPeer-reviewedCC BYFull textOrganic chemistryEurope PMCPMC
  2. Strategies for MOF Functionalization in Pyrotechnics and Propellants: Internal and Interfacial Approaches
    Aigerim Imash, Gaukhar Smagulova, Vladimir Efremov +3
    Molecules (Basel, Switzerland)Peer-reviewedCC BYFull textGeneral chemistryEurope PMC
  3. Stereodivergent Organocatalytic Glycosylation of 2-Deoxyglycosides
    Meizhe Liu, Aleksandar Mandić, Daan Hoogers +7
    ChemRxivPreprintLicence not statedGeneral chemistryChemRxiv
  4. Copper‐Catalyzed Regioconvergent and Stereodivergent Allylation and Alkenylation of Styrenes via Bromo‐Acyloxy Transposition
    Saghnik Saha, Upasana Mukherjee, Loay Bedda +4
    Advanced SciencePeer-reviewedCC BY 4.0Full textOrganic chemistryPMCEurope PMC
  5. Rh/Ru-Catalyzed Asymmetric One-Pot Sequential Hydrogenation: Stereodivergent Synthesis of Chiral 1,3-Amino Alcohol Derivatives
    Jingli He, Yicong Luo, Wanye Li +2
    JACS AuPeer-reviewedCC BY-NC-ND 4.0Full textInorganic & organometallic chemistryCrossrefEurope PMCPMC

Cite

BibTeXRIS
BibTeX
@article{ryutov2026regioselective,
  title = {{Regioselective and Stereodivergent C-H Functionalization of Internal Alkenes.}},
  author = {Elizabeth A Ryutov and Peter J Verardi and Song N Dang and Karina Targos and Leah C Garman and Zachary K Wickens},
  journal = {Journal of the American Chemical Society},
  year = {2026},
  month = oct,
  doi = {10.1021/jacs.6c17366},
  url = {https://europepmc.org/article/MED/42954562},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Regioselective and Stereodivergent C-H Functionalization of Internal Alkenes.
AU  - Elizabeth A Ryutov
AU  - Peter J Verardi
AU  - Song N Dang
AU  - Karina Targos
AU  - Leah C Garman
AU  - Zachary K Wickens
PY  - 2026
DA  - 2026/10/01
JO  - Journal of the American Chemical Society
DO  - 10.1021/jacs.6c17366
UR  - https://europepmc.org/article/MED/42954562
AB  - Herein, we introduce a new strategy for the regioselective and stereodivergent C-H functionalization of internal alkenes. We discovered that the regioselectivity of internal alkene thianthrenation is exceptionally electronically sensitive and can be controlled by native allylic and homoallylic functional groups. We also found that both alkenyl thianthrenium stereoisomers can be selectively accessed by using different workup conditions. While thianthrenation is typically stereoretentive, the addition of Cs2CO3 in the workup induces isomerization through reversible conjugate addition. We show that both stereoisomers of the alkenyl linchpins can be readily engaged in stereoretentive cross coupling reactions. This selective thianthrenation-coupling sequence introduces a generalizable platform for stereodefined trisubstituted alkene synthesis.
SN  - 0002-7863
SN  - 1520-5126
ER  -