Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2016, Volume: 57, Number: 1, Pages: 11-14 Pages count : 4 DOI: 10.1016/j.tetlet.2015.10.091

Authors

Mikhaylov Andrey A. ¹ , Dilman Alexander D. ¹ , Novikov Roman A. ¹ , Khoroshutina Yulia A. ¹ , Struchkova Marina I. ¹ , Arkhipov Dmitry E. ^2,3 , Nelyubina Yulia V. ² , Tabolin Andrey A. ¹ , Ioffe Sema L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str. 28, 119991 Moscow, Russian Federation
3	N. I. Pirogov Russian National Research Medical University, Ostrovityanova Str. 1, 117997 Moscow, Russian Federation

The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C–C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.

Mikhaylov A.A. , Dilman A.D. , Novikov R.A. , Khoroshutina Y.A. , Struchkova M.I. , Arkhipov D.E. , Nelyubina Y.V. , Tabolin A.A. , Ioffe S.L.
Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
Tetrahedron Letters. 2016. V.57. N1. P.11-14. DOI: 10.1016/j.tetlet.2015.10.091 WOS Scopus OpenAlex

≡ Web of science:	WOS:000368207600003
≡ Scopus:	2-s2.0-84949921007
≡ OpenAlex:	W2174727076