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Issue 15, 2018
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Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration

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Abstract

Disclosed herein is a novel and practical protocol for the radical-mediated phosphinoyl-functionalization of unactivated alkenes. The P-centered radicals are generated in the presence of TBHP under mild reaction conditions, which trigger the subsequent distal functional group migration. Both phosphine oxides and phosphonates are suitable precursors for the delivery of phosphinoyl radicals. As a result, phosphinoyl radicals along with another functional group such as heteroaryl, cyano, or imino are incorporated to alkenes concurrently. A wide range of synthetically valuable alkylphosphorus compounds are furnished in good yields.

Graphical abstract: Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration

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Publication details

The article was received on 06 Jun 2018, accepted on 27 Jun 2018 and first published on 28 Jun 2018


Article type: Research Article
DOI: 10.1039/C8QO00558C
Citation: Org. Chem. Front., 2018,5, 2370-2374
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    Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration

    D. Chen, Z. Wu, Y. Yao and C. Zhu, Org. Chem. Front., 2018, 5, 2370
    DOI: 10.1039/C8QO00558C

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