α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles

α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles

We report here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin...

Full description

Saved in:
Bibliographic Details
Main Authors: Ding, Zhenhua, Gao, Ke, Chen, Zhiyuan, Lu, Beili, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Subjects:
DRNTU::Science::Chemistry
Online Access:https://hdl.handle.net/10356/104402
http://hdl.handle.net/10220/16559
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Nanyang Technological University
Language: English
id sg-ntu-dr.10356-104402
record_format dspace
spelling sg-ntu-dr.10356-1044022020-03-07T12:34:58Z α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles Ding, Zhenhua Gao, Ke Chen, Zhiyuan Lu, Beili Yoshikai, Naohiko School of Physical and Mathematical Sciences DRNTU::Science::Chemistry We report here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization. 2013-10-17T06:19:52Z 2019-12-06T21:32:03Z 2013-10-17T06:19:52Z 2019-12-06T21:32:03Z 2013 2013 Journal Article Chen, Z., Lu, B., Ding, Z., Gao, K., & Yoshikai, N. (2013). α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles. Organic letters, 15(8), 1966-1969. https://hdl.handle.net/10356/104402 http://hdl.handle.net/10220/16559 10.1021/ol400638q en Organic letters
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry
spellingShingle DRNTU::Science::Chemistry
Ding, Zhenhua
Gao, Ke
Chen, Zhiyuan
Lu, Beili
Yoshikai, Naohiko
α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles
description We report here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ding, Zhenhua
Gao, Ke
Chen, Zhiyuan
Lu, Beili
Yoshikai, Naohiko
format Article
author Ding, Zhenhua
Gao, Ke
Chen, Zhiyuan
Lu, Beili
Yoshikai, Naohiko
author_sort Ding, Zhenhua
title α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles
title_short α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles
title_full α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles
title_fullStr α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles
title_full_unstemmed α-palladation of Imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-Allylimines to Pyrroles
title_sort α-palladation of imines as entry to dehydrogenative heck reaction: aerobic oxidative cyclization of n-allylimines to pyrroles
publishDate 2013
url https://hdl.handle.net/10356/104402
http://hdl.handle.net/10220/16559
_version_ 1681049335897260032

Similar Items