@article{105872a3ff6c4a65a06b55d10a4c422c,
title = "Iodane-Guided ortho C−H Allylation",
abstract = "A metal-free C−H allylation strategy is described to access diverse functionalized ortho-allyl-iodoarenes. The method employs hypervalent (diacetoxy)iodoarenes and proceeds through the iodane-guided “iodonio-Claisen” allyl transfer. The use of allylsilanes bearing electron-withdrawing functional groups unlocks the functionalization of a broad range of substrates, including electron-neutral and electron-poor rings. The resulting ortho-allylated iodoarenes are versatile building blocks, with examples of downstream transformation including a concise synthesis of the experimental antimitotic core of Dosabulin. DFT calculations shed additional light on the reaction mechanism, with notable aspects including the aromatic character of the transition-state structure for the [3,3] sigmatropic rearrangement, as well as the highly stereoconvergent nature of the trans-product formation.",
keywords = "C−H functionalization, allylic compounds, arenes, hypervalent compounds, rearrangements",
author = "Chen, {Wei W.} and Anton Cunillera and Dandan Chen and S{\'e}bastien Lethu and {L{\'o}pez de Moragas}, Albert and Jun Zhu and Miquel Sol{\`a} and Cuenca, {Ana B.} and Alexandr Shafir",
note = "Funding Information: This work was funded by MINECO (CTQ2017-86936-P, CTQ2017-85341-P) and AGAUR (2017 SGR 01051, 2017 SGR 00294, 2017 SGR 00039). Financial support from CSIC, URL (2019-URL_Proj-034) and IQS-Obra Social La Caixa (2017-URL-Intermac-010) is also gratefully acknowledged. IQS is acknowledged for a predoctoral fellowship to W. W. C. The State Scholarship Fund (No. 201906310040, D.C.) from the China Scholarship Council (CSC), the National Science Foundation of China (21573179, J.Z.), and the Top-Notch Young Talents Program of China (J.Z.) are also gratefully acknowledged. Funding Information: This work was funded by MINECO (CTQ2017‐86936‐P, CTQ2017‐85341‐P) and AGAUR (2017 SGR 01051, 2017 SGR 00294, 2017 SGR 00039). Financial support from CSIC, URL (2019‐URL_Proj‐034) and IQS‐Obra Social La Caixa (2017‐URL‐Intermac‐010) is also gratefully acknowledged. IQS is acknowledged for a predoctoral fellowship to W. W. C. The State Scholarship Fund (No. 201906310040, D.C.) from the China Scholarship Council (CSC), the National Science Foundation of China (21573179, J.Z.), and the Top‐Notch Young Talents Program of China (J.Z.) are also gratefully acknowledged. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",
year = "2020",
month = nov,
day = "2",
doi = "10.1002/anie.202009369",
language = "English",
volume = "59",
pages = "20201--20207",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "45",
}