2019
DOI: 10.1021/acs.orglett.9b01392
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Cobalt-Catalyzed Annulation Reactions of Alkylidenecyclopropanes: Access to Spirocyclopropanes at Room Temperature

Abstract: A bidentate chelation-assisted cobalt-catalyzed C­(sp2)–H activation and annulation of benzamides and alkylidenecyclopropanes (ACPs) has been realized. The unique reactivity of organocobalt species led to selective migratory insertion across the more electron-rich CC bond of the ACP followed by faster reductive elimination from the seven-membered cobaltacycle leading to spiro-dihydroisoquinoline derivatives with conservation of the cyclopropyl ring. The operationally simple reaction conditions allowed the C–H… Show more

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Cited by 48 publications
(22 citation statements)
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“…One year later, when they studied the Co(acac) 2 ‐catalyzed [4+2] annulation of N ‐(quinolin‐8‐yl)arenecarboxamides and 4‐chlorophenylmethylidenecyclopropane, they realized one example of the [4+2] annulation of N ‐(quinolin‐8‐yl)arylphosphinamides and 4‐chlorophenylmethylidenecyclopropane, affording the corresponding spiro cyclopropane‐benzo[ e ][1,2]azaphosphinine 1‐oxide (Scheme 25). [30] …”
Section: Synthesis Via Annulationsmentioning
confidence: 99%
See 1 more Smart Citation
“…One year later, when they studied the Co(acac) 2 ‐catalyzed [4+2] annulation of N ‐(quinolin‐8‐yl)arenecarboxamides and 4‐chlorophenylmethylidenecyclopropane, they realized one example of the [4+2] annulation of N ‐(quinolin‐8‐yl)arylphosphinamides and 4‐chlorophenylmethylidenecyclopropane, affording the corresponding spiro cyclopropane‐benzo[ e ][1,2]azaphosphinine 1‐oxide (Scheme 25). [30] …”
Section: Synthesis Via Annulationsmentioning
confidence: 99%
“…This is a convenient way to synthesize benzo ). [30] In 2017, Rao's research group extended the [4 + 2] annulation to allene derivatives. In the annulations, benzyl buta-2,3dienoate and ((buta-2,3-dien-1-yloxy)methyl)benzene yielded annuladducts with the same regiospecificity.…”
Section: Synthesis Via [4 + 2] Annulationmentioning
confidence: 99%
“…Due to their switchable high reactivity, alkylidenecyclopropanes (ACPs) 46 have attracted considerable interest, which could be utilized as uncommon π‐organic components in C−H/N‐H functionalization. Recently, the Volla group revealed ACPs as viable coupling partners in the annulation reaction with benzamides (Scheme ) . This protocol provided facile access to spiro‐heterocycles with conservation of the highly strained cyclopropyl ring.…”
Section: Alkyne Annulationmentioning
confidence: 99%
“…In spite of the above methods for the C2-amination, the establishment of a simple, efficient and atom-economical method for the synthesis of 2-triazolylquinoline derivatives is highly desired. The continuous interest and efforts of our group for the derivatization of quinoline moieties [57] and use of N-sulfonyl-1,2,3-triazoles as heterocyclic precursors encouraged us to develop a new strategy for the regioselective C2-triazolylation of quinoline N-oxide under mild reaction conditions (Scheme 1b) [58][59][60][61][62].…”
Section: Introductionmentioning
confidence: 99%