Divergent Construction of Polycyclic Frameworks Enabled by Sequential Ru-Catalyzed [2 + 2 + 2] Cycloaddition of Iododiynes and Pd/Norbornene-Mediated Catellani-Type Annulation
The Ru-catalyzed [2 + 2 + 2] cycloaddition of iododiynes with <i>ex situ</i> generated acetylene gas afforded bicyclic iodobenzenes in high yields. The obtained bicyclic iodobenzenes were subsequently subjected to Pd/NBE-mediated Catellani-type annulations, yielding a variety of polycyclic products. Control experiments using a deuterated bicyclic iodobenzene, which was prepared using acetylene-<i>d</i><sub>2</sub> <i>ex situ</i> generated from CaC<sub>2</sub> and D<sub>2</sub>O, revealed that the C-H activation step leading to a palladacycle intermediate is rate-determining when ethyl (<i>E</i>)-6-bromohex-2-enoate was used as a reaction partner.
Authors
- Kenichi Yoshimura (ORCID: https://orcid.org/0000-0001-7393-6932)
- Yoshihiko Yamamoto (ORCID: https://orcid.org/0000-0001-8544-6324)
- Takeshi Yasui (ORCID: https://orcid.org/0000-0002-7630-8736)
- Yutaro Hayashi
Institutions
- Office of Basic Energy Sciences (US)
- Nagoya University (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c03804
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00