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Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold

Anastasia Vepreva, Alexander S. Bunev, Andrey Yu. Kudinov, Grigory Kantin, Mikhail Krasavin and Dmitry Dar’in

Beilstein J. Org. Chem. 2022, 18, 533–538. https://doi.org/10.3762/bjoc.18.55

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Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold

Anastasia Vepreva, Alexander S. Bunev, Andrey Yu. Kudinov, Grigory Kantin, Mikhail Krasavin and Dmitry Dar’in

Beilstein J. Org. Chem. 2022, 18, 533–538. https://doi.org/10.3762/bjoc.18.55

How to Cite

Vepreva, A.; Bunev, A. S.; Kudinov, A. Y.; Kantin, G.; Krasavin, M.; Dar’in, D. Beilstein J. Org. Chem. 2022, 18, 533–538. doi:10.3762/bjoc.18.55

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TY  - JOUR
A1  - Vepreva, Anastasia
A1  - Bunev, Alexander S.
A1  - Kudinov, Andrey Yu.
A1  - Kantin, Grigory
A1  - Krasavin, Mikhail
A1  - Dar’in, Dmitry
T1  - Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 533
EP  - 538
SN  - 1860-5397
DO  - 10.3762/bjoc.18.55
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.55
KW  - diazo arylidene succinimides
KW  - dibenzoazulenodipyrroles
KW  - indenopyrroles
KW  - Rh2(esp)2-catalyzed decomposition
KW  - unsymmetrical dimers
N2  - Formation of unusual unsymmetrical dimers or/and indenes via Rh2(esp)2-catalyzed decomposition of 3-diazo-2-arylidenesuccinimides has been investigated. The reaction proceeded under mild conditions, and its result was shown to strongly depend on the nature of the substituents in the diazo substrate. The new reaction provides access to dibenzoazulenodipyrrole and indenopyrrole derivatives in moderate to high yield. Dibenzoazulenodipyrroles bearing alkyl substituents at the nitrogen atom showed pronounced cytotoxocity against the A549 human lung adenocarcinoma cell line while N-aryl analogs were non-cytotoxic.
ER  -

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Laha, D.; Bankar, O. S.; Santra, S.; Navale, B. S.; Ghosh, D.; Bhat, R. G. Photosensitizer-Free Photoinduced Ground-State Triplet Carbene-Assisted Persistent Aryloxy Radical Generation via Hydrogen Atom Transfer. Organic letters 2024, 26, 8674–8679. doi:10.1021/acs.orglett.4c02717
Kazantsev, A.; Rodionov, I. A.; Bakulina, O.; Kantin, G.; Dar'in, D.; Krasavin, M. Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran. Catalysts 2023, 13, 428. doi:10.3390/catal13020428
Vepreva, A.; Yanovich, A.; Dar'in, D.; Kantin, G.; Bunev, A.; Krasavin, M. A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition. Beilstein journal of organic chemistry 2022, 18, 1649–1655. doi:10.3762/bjoc.18.177

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