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

1 Scopus citations

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

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.",

author = "Rynders, \{Kathryn J.\} and Huh, \{Daniel N.\} and Stuart, \{Zoe E.\} and Vang, \{Zoua Pa\} and Tonks, \{Ian A.\}",

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doi = "10.1021/acs.organomet.4c00354",

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AU - Rynders, Kathryn J.

AU - Huh, Daniel N.

AU - Stuart, Zoe E.

AU - Vang, Zoua Pa

AU - Tonks, Ian A.

PY - 2024/9/23

Y1 - 2024/9/23

N2 - 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.

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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UR - https://www.scopus.com/pages/publications/85203841209#tab=citedBy

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SN - 0276-7333

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JF - Organometallics

IS - 18

ER -

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

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