Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes

A cobalt-diphosphine catalyst has been found to promote a selective 1:2 coupling reaction between aldehydes and allenes to form β,δ-dialkylidene ketones, featuring skipped diene moieties, with high regioselectivities and stereoselectivities. The reaction is distinct from previously reported, rhodium...

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Main Authors:	Ding, Wei, Ho, Terence Yan King, Okuda, Yasuhiro, Wijaya, Christopher Kevin, Tan, Zheng Hao, Yoshikai, Naohiko
Other Authors:	School of Physical and Mathematical Sciences
Format:	Article
Language:	English
Published:	2020
Subjects:	Science::Chemistry Hydrocarbons Aldehydes
Online Access:	https://hdl.handle.net/10356/145049
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Institution:	Nanyang Technological University
Language:	English

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spelling	sg-ntu-dr.10356-1450492023-02-28T19:27:20Z Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes Ding, Wei Ho, Terence Yan King Okuda, Yasuhiro Wijaya, Christopher Kevin Tan, Zheng Hao Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Hydrocarbons Aldehydes A cobalt-diphosphine catalyst has been found to promote a selective 1:2 coupling reaction between aldehydes and allenes to form β,δ-dialkylidene ketones, featuring skipped diene moieties, with high regioselectivities and stereoselectivities. The reaction is distinct from previously reported, rhodium-catalyzed aldehyde-allene 1:2 coupling to afford β,γ-dialkylidene ketones bearing 1,3-diene moieties. The present hydroacylative dimerization involves a unique allene/allene oxidative cyclization mode to form a C1-C2 linkage between the allene molecules. Ministry of Education (MOE) Nanyang Technological University Accepted version We acknowledge the Ministry of Education (Singapore) and Nanyang Technological University (Nos. MOE2016-T2-2-043 and RG114/18) for financial support of this work. This work was also partially supported by JSPS KAKENHI (Grant Nos.JP18H04430 in Middle Molecular Strategy (Y.O.) and JP19K15574 (Y.O.)), Okayama Foundation of Science and Technology (Y.O.), Promotion and Mutual Aid Corporationfor Private Schools of Japan (Y.O.), and OUS Research Project (OUS-RP-19-4 to Y.O.). We thank Dr. Yongxin Li (NanyangTechnological University) for his assistance with the X-ray crystallographic analysis. 2020-12-09T06:40:43Z 2020-12-09T06:40:43Z 2019 Journal Article Ding, W., Ho, T. Y. K., Okuda, Y., Wijaya, C. K., Tan, Z. H., & Yoshikai, N. (2019). Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes. Organic Letters, 21(15), 6173-6178. doi:10.1021/acs.orglett.9b02465 1523-7060 https://hdl.handle.net/10356/145049 10.1021/acs.orglett.9b02465 31334661 15 21 6173 6178 en MOE2016-T2-2-043 RG114/18 Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b02465 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 Hydrocarbons Aldehydes
spellingShingle	Science::Chemistry Hydrocarbons Aldehydes Ding, Wei Ho, Terence Yan King Okuda, Yasuhiro Wijaya, Christopher Kevin Tan, Zheng Hao Yoshikai, Naohiko Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes
description	A cobalt-diphosphine catalyst has been found to promote a selective 1:2 coupling reaction between aldehydes and allenes to form β,δ-dialkylidene ketones, featuring skipped diene moieties, with high regioselectivities and stereoselectivities. The reaction is distinct from previously reported, rhodium-catalyzed aldehyde-allene 1:2 coupling to afford β,γ-dialkylidene ketones bearing 1,3-diene moieties. The present hydroacylative dimerization involves a unique allene/allene oxidative cyclization mode to form a C1-C2 linkage between the allene molecules.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Ding, Wei Ho, Terence Yan King Okuda, Yasuhiro Wijaya, Christopher Kevin Tan, Zheng Hao Yoshikai, Naohiko
format	Article
author	Ding, Wei Ho, Terence Yan King Okuda, Yasuhiro Wijaya, Christopher Kevin Tan, Zheng Hao Yoshikai, Naohiko
author_sort	Ding, Wei
title	Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes
title_short	Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes
title_full	Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes
title_fullStr	Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes
title_full_unstemmed	Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes
title_sort	cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes
publishDate	2020
url	https://hdl.handle.net/10356/145049
_version_	1759855356389883904

Cobalt-catalyzed hydroacylative dimerization of allenes leading to skipped dienes

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