Diastereoselective Homocoupling of Benzylic C(sp<sup>3</sup>)–H Bonds Enabled by Halogen Transfer
A transition-metal- and harsh-oxidant-free strategy for diastereoselective homocoupling of benzylic α-boryl carbanions has been developed. Central to this methodology is the ability of the halogen transfer reagent to seamlessly integrate halogenation and substitution within a compatible process. Additionally, this methodology is also applicable to the homocoupling of diarylmethanes and alkylheteroarenes. Substrates bearing oxidatively sensitive functional groups were well-tolerated. Preliminary studies suggest that the hydrogen bond between two boryl groups contributes to the high diastereoselectivities.
Authors
- Xirong Liu (ORCID: https://orcid.org/0000-0003-2405-7936)
- Miao Zhan (ORCID: https://orcid.org/0000-0002-6492-5104)
- Shu‐Ping Luo (ORCID: https://orcid.org/0000-0002-8108-4132)
- Liang Xu (ORCID: https://orcid.org/0000-0002-7939-8108)
- Xue Zhao (ORCID: https://orcid.org/0000-0001-9281-7680)
- Xin An (ORCID: https://orcid.org/0009-0002-7544-1452)
Institutions
- Shihezi University (CN)
- Northwestern Polytechnical University (CN)
- Xinjiang Production and Construction Corps (CN)
- Research & Development Institute (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-18
- DOI
- https://doi.org/10.1021/acs.orglett.4c03377
- Citations
- 2
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- National Natural Science Foundation of China
- Key Research and Development Projects of Shaanxi Province
- Basic and Applied Basic Research Foundation of Guangdong Province