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Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes

preprint
revised on 30.10.2018 and posted on 31.10.2018 by Jeishla Melendez Matos, Suhelen Vásquez-Céspedes, Jieyu Gu, Takuya Oguma, Ryan Shenvi
Radical hydrofunctionalization occurs with ease using met-al-hydride atom transfer (MHAT) catalysis to couple alkenes and competent radicalophilic electrophiles. Traditional two-electron electrophiles have remained unreactive. Herein we report the addition of electronically-unbiased olefins into imines and aldehydes. Iron-catalysis allows addition of alkyl-substituted olefins into imines through the intermediacy of free-radicals, whereas a combination of catalytic Co(Salt-Bu,t-Bu) and chromium salts enable a branch-selective coupling of olefins and aldehydes through the formation of a putative alkyl chromium intermediate.

History

Email Address of Submitting Author

rshenvi@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0001-8353-6449

Declaration of Conflict of Interest

No conflict of interest

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