Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate

Ghosh, Koushik; Nishii, Yuji; Miura, Masahiro

ACS Catalysis, 2019, 9(12), 11455-11460

Number of Access:149（2025-06-29 13:23 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92818

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Title
Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate
Creator
CreatorName
Ghosh, Koushik
NRID
1000070773787 1000070773787
ORCID
0000-0002-6824-0639 0000-0002-6824-0639
researchmap permalink
y_nishii y_nishii
Scopus Author ID
55233363700 55233363700
CreatorName
Nishii, Yuji
NRID
1000020183626 1000020183626
ORCID
0000-0001-8288-6439 0000-0001-8288-6439
researchmap permalink
read0013936 read0013936
Scopus Author ID
7402799909 7402799909
CreatorName
Miura, Masahiro
Subject
acetylene
C-H functionalization
cyclization
N-heterocycles
rhodium
Description
Ghosh K., Nishii Y., Miura M.. Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as an Oxidizing Acetylene Surrogate. ACS Catalysis. 9(12), 11455-11460, (2019), 6 December 2019; ©2019 American Chemical Society. https://doi.org/10.1021/acscatal.9b04254.
Abstract
Transition-metal-catalyzed C–H activation and subsequent oxidative cyclization with alkynes has been a pow-erful tool for the synthesis of polycyclic aromatic compounds. Despite the substantial progress in this field, it is still a significant challenge to establish synthetic methodologies for the construction of non-substituted vinylene-fused aromatics. We herein report a Rh(III)-catalyzed C–H/N–H annulation with vinylene carbonate as an acetylene surrogate. Vinylene carbonate also acts as an internal oxidant to regenerate the Rh(III) species in situ; thus no external oxidant is required to trigger the oxidative annulation. This protocol is applicable to the direct synthesis of various N-heteroaromatics.
Publisher
American Chemical Societyservice
Source Title
ACS Catalysis
Volume (Issue)
9(12)
Page
11455-11460
Date of Issued
2019-12-06
Language
English
Handle URL
https://hdl.handle.net/11094/92818
eISSN
21555435
NCID
AA12599706
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acscatal.9b04254
Access Rights
open access
CopyRight
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, © 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/acscatal.9b04254.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article