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A Directive Ni Catalyst Overrides Conventional Site-Selectivity in Pyridine C–H Alkenylation

preprint
submitted on 18.11.2020, 03:44 and posted on 18.11.2020, 12:58 by Tao Zhang, Yu-Xin Luan, Nelson Lam, Jiang-Fei Li, Yue Li, Mengchun Ye, jin-quan yu
A remote C3–H activation of pyridine-containing substrates can be achieved with a directive Ni catalyst. The bifunctional NHC ligand incorporates an Al-binding side-arm that recruits and orients the substrate leading to the assembly of the requisite macrocyclophane transition state through reversible coordination. This assembly not only induces the reactivity of the otherwise unreactive Ni catalyst, but also overrides the intrinsic C2/C4 electronic bias of the Al-bound pyridine substrate, allowing for the first time, the C3 alkenylation of a variety of pyridine and heteroarene substrates as the limiting reagent.

Funding

National Natural Science Foundation of China (91856104, 21871145 and 21672107)

Fundamental Research Funds for the Central Universities (63191601)

National Institute of General Medical Sciences Grant R01GM102265

History

Email Address of Submitting Author

yu200@scripps.edu

Institution

The Scripps Research Institute

Country

United States

ORCID For Submitting Author

0000-0003-3560-5774

Declaration of Conflict of Interest

No conflict of interest

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