Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles

Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2024, Volume: 26, Number: 38, Pages: 8177-8182 Pages count : 6 DOI: 10.1021/acs.orglett.4c03106

Authors

Shorokhov Vitaly V. ¹ , Chabuka Beauty K. ² , Tikhonov Timur P. ¹ , Filippova Anastasia V. ¹ , Zhokhov Sergey S. ¹ , Tafeenko Victor A. ¹ , Andreev Ivan A. ³ , Ratmanova Nina K. ³ , Uchuskin Maxim G. ⁴ , Trushkov Igor V. ⁵ , Alabugin Igor V. ² , Ivanova Olga A. ¹

Affiliations

1	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russia
2	Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, United States
3	Organic Chemistry Department, Science Faculty, Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya 6, Moscow 117198, Russia
4	Department of Chemistry, Perm State University, Bukireva 15, Perm 614990, Russia
5	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia

Here, we present a new approach for the activation of donor–acceptor cyclopropanes in ring-opening reactions, which does not require the use of a Lewis or Brønsted acid as a catalyst. Donor–acceptor cyclopropanes containing a phenolic group as the donor undergo deprotonation and isomerization to form the corresponding quinone methides. This innovative strategy was applied to achieve (4 + 1)-annulation of cyclopropanes with sulfur ylides, affording functionalized dihydrobenzofurans. Additionally, the generated ortho- and para-(aza)quinone methides can be trapped by various CH-acids.

Shorokhov V.V. , Chabuka B.K. , Tikhonov T.P. , Filippova A.V. , Zhokhov S.S. , Tafeenko V.A. , Andreev I.A. , Ratmanova N.K. , Uchuskin M.G. , Trushkov I.V. , Alabugin I.V. , Ivanova O.A.
Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles
Organic Letters. 2024. V.26. N38. P.8177-8182. DOI: 10.1021/acs.orglett.4c03106 WOS Scopus OpenAlex

Web of science:	WOS:001310753000001
Scopus:	2-s2.0-85203819226
OpenAlex:	W4402472434

DB	Citing
OpenAlex	10
Scopus	6
Web of science	9