CuII-Catalyzed Coupling with Two Ynone Units by Selective Triple and Sigma C-C and C-H Bond Cleavages

Jiang Nan; Jiawen Zhang; Yan Hu; Chao Wang; Tingting Wang; Weitao Wang; Yangmin Ma; Michal Szostak

doi:10.1021/acs.orglett.1c00371

CuII-Catalyzed Coupling with Two Ynone Units by Selective Triple and Sigma C-C and C-H Bond Cleavages

Jiang Nan, Jiawen Zhang, Yan Hu, Chao Wang, Tingting Wang, Weitao Wang, Yangmin Ma, Michal Szostak

Rutgers Newark, Chemistry

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

13 Scopus citations

Abstract

We report a new copper-catalyzed [2 + 2 + 1] annulation process through the selective cleavage of sigma and triple C-C and C-H bonds using two ynone units. This new methodology involves breaking multiple chemical bonds in a single operation, including CC, C-C, C-H, and N-O. These high-value adducts lead to a diverse collection of synthetically challenging trisubstituted indolizines by the simultaneous engagement of different bond-breaking events and show excellent fluorescence in green aqueous solutions.

Original language	English (US)
Pages (from-to)	1928-1933
Number of pages	6
Journal	Organic letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.1c00371
State	Published - Mar 5 2021

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "CuII-Catalyzed Coupling with Two Ynone Units by Selective Triple and Sigma C-C and C-H Bond Cleavages",

abstract = "We report a new copper-catalyzed [2 + 2 + 1] annulation process through the selective cleavage of sigma and triple C-C and C-H bonds using two ynone units. This new methodology involves breaking multiple chemical bonds in a single operation, including CC, C-C, C-H, and N-O. These high-value adducts lead to a diverse collection of synthetically challenging trisubstituted indolizines by the simultaneous engagement of different bond-breaking events and show excellent fluorescence in green aqueous solutions.",

author = "Jiang Nan and Jiawen Zhang and Yan Hu and Chao Wang and Tingting Wang and Weitao Wang and Yangmin Ma and Michal Szostak",

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T1 - CuII-Catalyzed Coupling with Two Ynone Units by Selective Triple and Sigma C-C and C-H Bond Cleavages

AU - Nan, Jiang

AU - Zhang, Jiawen

AU - Hu, Yan

AU - Wang, Chao

AU - Wang, Tingting

AU - Wang, Weitao

AU - Ma, Yangmin

AU - Szostak, Michal

PY - 2021/3/5

Y1 - 2021/3/5

N2 - We report a new copper-catalyzed [2 + 2 + 1] annulation process through the selective cleavage of sigma and triple C-C and C-H bonds using two ynone units. This new methodology involves breaking multiple chemical bonds in a single operation, including CC, C-C, C-H, and N-O. These high-value adducts lead to a diverse collection of synthetically challenging trisubstituted indolizines by the simultaneous engagement of different bond-breaking events and show excellent fluorescence in green aqueous solutions.

AB - We report a new copper-catalyzed [2 + 2 + 1] annulation process through the selective cleavage of sigma and triple C-C and C-H bonds using two ynone units. This new methodology involves breaking multiple chemical bonds in a single operation, including CC, C-C, C-H, and N-O. These high-value adducts lead to a diverse collection of synthetically challenging trisubstituted indolizines by the simultaneous engagement of different bond-breaking events and show excellent fluorescence in green aqueous solutions.

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AN - SCOPUS:85101610772

SN - 1523-7060

VL - 23

SP - 1928

EP - 1933

JO - Organic letters

JF - Organic letters

IS - 5

ER -

CuII-Catalyzed Coupling with Two Ynone Units by Selective Triple and Sigma C-C and C-H Bond Cleavages

Abstract

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