Nitrosoarenes Implement Cascade Cyclization of 1-Allenyl-2-alkynylbenzenes through Diradical Mechanism

Chandrima Maitra; Prakash D. Jadhav; Debashis Barik; Yeu Shiuan Ho; Chu Chun Cheng; Mu Jeng Cheng; Yun Wei Chiang; Rai Shung Liu

doi:10.1021/acs.orglett.2c03884

Nitrosoarenes Implement Cascade Cyclization of 1-Allenyl-2-alkynylbenzenes through Diradical Mechanism

Chandrima Maitra
, Prakash D. Jadhav
, Debashis Barik
, Yeu Shiuan Ho
, Chu Chun Cheng
, Mu Jeng Cheng
, Yun Wei Chiang
, Rai Shung Liu

Department of Chemistry

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

7 Citations (Scopus)

Abstract

This work reports cascade cyclization between 1-allenyl-2-alkynylbenzenes and nitrosoarenes. When these two components reacted alone under N₂, N,O-functionalized indane-fused isoxazolidines 3 were obtained selectively. DFT calculations verify that this reaction sequence involves unprecedented nitrone/alkyne cycloadditions, followed by diradical rearrangement.

Original language	English
Pages (from-to)	82-86
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.2c03884
Publication status	Published - 2023 Jan 13

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c03884

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title = "Nitrosoarenes Implement Cascade Cyclization of 1-Allenyl-2-alkynylbenzenes through Diradical Mechanism",

abstract = "This work reports cascade cyclization between 1-allenyl-2-alkynylbenzenes and nitrosoarenes. When these two components reacted alone under N2, N,O-functionalized indane-fused isoxazolidines 3 were obtained selectively. DFT calculations verify that this reaction sequence involves unprecedented nitrone/alkyne cycloadditions, followed by diradical rearrangement.",

author = "Chandrima Maitra and Jadhav, \{Prakash D.\} and Debashis Barik and Ho, \{Yeu Shiuan\} and Cheng, \{Chu Chun\} and Cheng, \{Mu Jeng\} and Chiang, \{Yun Wei\} and Liu, \{Rai Shung\}",

note = "Funding Information: We thank the Ministry of Education (MOE 111QR001I5) and the National Science and Technology Council (NSTC 111-2634-F-007-007), Taiwan, for their financial support of this work. Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2023",

month = jan,

day = "13",

doi = "10.1021/acs.orglett.2c03884",

language = "English",

volume = "25",

pages = "82--86",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Nitrosoarenes Implement Cascade Cyclization of 1-Allenyl-2-alkynylbenzenes through Diradical Mechanism

AU - Maitra, Chandrima

AU - Jadhav, Prakash D.

AU - Barik, Debashis

AU - Ho, Yeu Shiuan

AU - Cheng, Chu Chun

AU - Cheng, Mu Jeng

AU - Chiang, Yun Wei

AU - Liu, Rai Shung

N1 - Funding Information: We thank the Ministry of Education (MOE 111QR001I5) and the National Science and Technology Council (NSTC 111-2634-F-007-007), Taiwan, for their financial support of this work. Publisher Copyright: © 2022 American Chemical Society.

PY - 2023/1/13

Y1 - 2023/1/13

N2 - This work reports cascade cyclization between 1-allenyl-2-alkynylbenzenes and nitrosoarenes. When these two components reacted alone under N2, N,O-functionalized indane-fused isoxazolidines 3 were obtained selectively. DFT calculations verify that this reaction sequence involves unprecedented nitrone/alkyne cycloadditions, followed by diradical rearrangement.

AB - This work reports cascade cyclization between 1-allenyl-2-alkynylbenzenes and nitrosoarenes. When these two components reacted alone under N2, N,O-functionalized indane-fused isoxazolidines 3 were obtained selectively. DFT calculations verify that this reaction sequence involves unprecedented nitrone/alkyne cycloadditions, followed by diradical rearrangement.

UR - https://www.scopus.com/pages/publications/85145310481

UR - https://www.scopus.com/pages/publications/85145310481#tab=citedBy

U2 - 10.1021/acs.orglett.2c03884

DO - 10.1021/acs.orglett.2c03884

M3 - Article

C2 - 36573784

AN - SCOPUS:85145310481

SN - 1523-7060

VL - 25

SP - 82

EP - 86

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Nitrosoarenes Implement Cascade Cyclization of 1-Allenyl-2-alkynylbenzenes through Diradical Mechanism

Abstract

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