Flash Communication: Ti-Catalyzed “Interrupted” Cascading Hydroamination of 1,6- and 1,7-En-ynes

Kathryn J. Rynders; Daniel N. Huh; Zoe E. Stuart; Zoua Pa Vang; Ian A. Tonks

doi:10.1021/acs.organomet.4c00354

Flash Communication: Ti-Catalyzed “Interrupted” Cascading Hydroamination of 1,6- and 1,7-En-ynes

Kathryn J. Rynders, Daniel N. Huh, Zoe E. Stuart, Zoua Pa Vang, Ian A. Tonks

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

Abstract

Herein, we report a new hydroaminative cyclization for 1,6- and 1,7-en-ynes using a simple Ti imido precatalyst, [py₂TiCl₂(NPh)]₂. The well-known Ti imido + alkyne [2 + 2] azatitanacyclobutadiene cycloadduct intermediate can be further intercepted via insertion by tethered alkenes, followed by protonolysis of the resultant metallacycle to yield α-carbocyclic imine products through cascading C-N and C-C bond formation.

Original language	English (US)
Pages (from-to)	1952-1955
Number of pages	4
Journal	Organometallics
Volume	43
Issue number	18
DOIs	https://doi.org/10.1021/acs.organomet.4c00354
State	Published - Sep 23 2024

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© 2024 American Chemical Society.

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abstract = "Herein, we report a new hydroaminative cyclization for 1,6- and 1,7-en-ynes using a simple Ti imido precatalyst, [py2TiCl2(NPh)]2. The well-known Ti imido + alkyne [2 + 2] azatitanacyclobutadiene cycloadduct intermediate can be further intercepted via insertion by tethered alkenes, followed by protonolysis of the resultant metallacycle to yield α-carbocyclic imine products through cascading C-N and C-C bond formation.",

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AU - Stuart, Zoe E.

AU - Vang, Zoua Pa

AU - Tonks, Ian A.

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AB - Herein, we report a new hydroaminative cyclization for 1,6- and 1,7-en-ynes using a simple Ti imido precatalyst, [py2TiCl2(NPh)]2. The well-known Ti imido + alkyne [2 + 2] azatitanacyclobutadiene cycloadduct intermediate can be further intercepted via insertion by tethered alkenes, followed by protonolysis of the resultant metallacycle to yield α-carbocyclic imine products through cascading C-N and C-C bond formation.

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Flash Communication: Ti-Catalyzed “Interrupted” Cascading Hydroamination of 1,6- and 1,7-En-ynes

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