NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives

Hong Ji; Juan Zou; Chengli Mou; Yonggui Liu; Shi Chao Ren; Yonggui Robin Chi

doi:10.1039/d3cc00999h

NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives

Hong Ji, Juan Zou, Chengli Mou, Yonggui Liu, Shi Chao Ren^*, Yonggui Robin Chi^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp³ (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that our products exhibit superior in vitro bioactivities against two plant pathogens to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC).

Original language	English
Pages (from-to)	6351-6354
Number of pages	4
Journal	Chemical Communications
Volume	59
Issue number	42
DOIs	https://doi.org/10.1039/d3cc00999h
Publication status	Published - Apr 14 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/d3cc00999h

Cite this

@article{42795d00a0ed4b46bca47b3be8252064,

title = "NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives",

abstract = "An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that our products exhibit superior in vitro bioactivities against two plant pathogens to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC).",

author = "Hong Ji and Juan Zou and Chengli Mou and Yonggui Liu and Ren, {Shi Chao} and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

month = apr,

day = "14",

doi = "10.1039/d3cc00999h",

language = "English",

volume = "59",

pages = "6351--6354",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "42",

}

TY - JOUR

T1 - NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives

AU - Ji, Hong

AU - Zou, Juan

AU - Mou, Chengli

AU - Liu, Yonggui

AU - Ren, Shi Chao

AU - Chi, Yonggui Robin

PY - 2023/4/14

Y1 - 2023/4/14

N2 - An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that our products exhibit superior in vitro bioactivities against two plant pathogens to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC).

AB - An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that our products exhibit superior in vitro bioactivities against two plant pathogens to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC).

UR - http://www.scopus.com/inward/record.url?scp=85159166457&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85159166457&partnerID=8YFLogxK

U2 - 10.1039/d3cc00999h

DO - 10.1039/d3cc00999h

M3 - Article

C2 - 37158205

AN - SCOPUS:85159166457

SN - 1359-7345

VL - 59

SP - 6351

EP - 6354

JO - Chemical Communications

JF - Chemical Communications

IS - 42

ER -

NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this