TY - JOUR
T1 - Electrophilic Trapping of Semibenzenes
AU - Boldrini, Cosimo
AU - Reis, Marta Castiñeira
AU - Harutyunyan, Syuzanna R.
N1 - Funding Information:
Financial support from the European Research Council (S.R.H. Grant no. 773264, LACOPAROM) is acknowledged. M.C.R. would like to thank the Centro de Supercomputación de Galicia (CESGA) for the free allocation of computational resources and the Xunta de Galicia (Galicia, Spain) for financial support through the ED481B-Axudas de apoio á etapa de formación posdoutoral (modalidade A) fellowship.
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/10/7
Y1 - 2022/10/7
N2 - In this work, we demonstrate how allylative dearomatization of benzyl chlorides can provide direct access to a variety of semibenzenes. These scaffolds behave as highly reactive nucleophiles in the presence of carbocations. In addition, semibenzenes are susceptible to intramolecular rearrangements rendering a broad scope of functionalized arenes. An analysis of this new reactivity is reported, as well as the rationale behind the observed intramolecular reorganizations.
AB - In this work, we demonstrate how allylative dearomatization of benzyl chlorides can provide direct access to a variety of semibenzenes. These scaffolds behave as highly reactive nucleophiles in the presence of carbocations. In addition, semibenzenes are susceptible to intramolecular rearrangements rendering a broad scope of functionalized arenes. An analysis of this new reactivity is reported, as well as the rationale behind the observed intramolecular reorganizations.
UR - https://www.scopus.com/pages/publications/85138668557
U2 - 10.1021/acs.joc.2c01331
DO - 10.1021/acs.joc.2c01331
M3 - Article
AN - SCOPUS:85138668557
SN - 0022-3263
VL - 87
SP - 12772
EP - 12782
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -