Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes

Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes

An intermolecular [2+2] cycloaddition reaction between an alkyne and an allene is reported. In the presence of a cobalt(I)/diphosphine catalyst, a near equimolar mixture of the alkyne and allene is converted into a 3-alkylidenecyclobutene derivative in good yield with high regioselectivity. The reac...

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Main Authors: Ding, Wei, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry
Alkynes
Allenes
Online Access:https://hdl.handle.net/10356/143608
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1436082023-02-28T19:23:01Z Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes Ding, Wei Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Alkynes Allenes An intermolecular [2+2] cycloaddition reaction between an alkyne and an allene is reported. In the presence of a cobalt(I)/diphosphine catalyst, a near equimolar mixture of the alkyne and allene is converted into a 3-alkylidenecyclobutene derivative in good yield with high regioselectivity. The reaction tolerates a variety of internal alkynes and mono- or disubstituted allenes bearing various functional groups. The reaction is proposed to involve regioselective oxidative cyclization of the alkyne and allene to form a 4-alkylidenecobaltacyclopentene intermediate, with subsequent C-C reductive elimination. Ministry of Education (MOE) Accepted version This work was supported by the Ministry of Education (Singapore) and Nanyang Technological University (MOE2016-T2-2-043). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance with the X-ray crystallographic analysis. 2020-09-14T03:17:44Z 2020-09-14T03:17:44Z 2019 Journal Article Ding, W., & Yoshikai, N. (2019). Cobalt‐Catalyzed Intermolecular [2+2] Cycloaddition between Alkynes and Allenes. Angewandte Chemie International Edition, 58(8), 2500–2504. doi:10.1002/anie.201813283 0044-8249 https://hdl.handle.net/10356/143608 10.1002/anie.201813283 30614605 8 58 2500 2504 en Angewandte Chemie This is the accepted version of the following article: Ding, W., & Yoshikai, N. (2019). Cobalt‐Catalyzed Intermolecular [2+2] Cycloaddition between Alkynes and Allenes. Angewandte Chemie International Edition, 58(8), 2500–2504., which has been published in final form at doi:10.1002/anie.201813283. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [https://authorservices.wiley.com/authorresources/Journal-Authors/licensing/self-archiving.html]. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Alkynes
Allenes
spellingShingle Science::Chemistry
Alkynes
Allenes
Ding, Wei
Yoshikai, Naohiko
Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes
description An intermolecular [2+2] cycloaddition reaction between an alkyne and an allene is reported. In the presence of a cobalt(I)/diphosphine catalyst, a near equimolar mixture of the alkyne and allene is converted into a 3-alkylidenecyclobutene derivative in good yield with high regioselectivity. The reaction tolerates a variety of internal alkynes and mono- or disubstituted allenes bearing various functional groups. The reaction is proposed to involve regioselective oxidative cyclization of the alkyne and allene to form a 4-alkylidenecobaltacyclopentene intermediate, with subsequent C-C reductive elimination.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ding, Wei
Yoshikai, Naohiko
format Article
author Ding, Wei
Yoshikai, Naohiko
author_sort Ding, Wei
title Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes
title_short Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes
title_full Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes
title_fullStr Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes
title_full_unstemmed Cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes
title_sort cobalt-catalyzed intermolecular [2+2] cycloaddition between alkynes and allenes
publishDate 2020
url https://hdl.handle.net/10356/143608
_version_ 1759854236327215104

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