UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides

Ming Chen; Chao Yang; Yanpei Wang; Dazhi Li; Wujiong Xia

doi:10.1021/acs.orglett.6b00878

UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides

Ming Chen
, Chao Yang
, Yanpei Wang
, Dazhi Li
, Wujiong Xia^*

^*Corresponding author for this work

Harbin Institute of Technology Shenzhen

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

39 Scopus citations

Abstract

A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.

Original language	English
Pages (from-to)	2280-2283
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.6b00878
State	Published - 6 May 2016
Externally published	Yes

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title = "UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides",

abstract = "A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.",

author = "Ming Chen and Chao Yang and Yanpei Wang and Dazhi Li and Wujiong Xia",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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doi = "10.1021/acs.orglett.6b00878",

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T1 - UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides

AU - Chen, Ming

AU - Yang, Chao

AU - Wang, Yanpei

AU - Li, Dazhi

AU - Xia, Wujiong

PY - 2016/5/6

Y1 - 2016/5/6

N2 - A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.

AB - A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.

UR - https://www.scopus.com/pages/publications/84969677884

U2 - 10.1021/acs.orglett.6b00878

DO - 10.1021/acs.orglett.6b00878

M3 - 文章

AN - SCOPUS:84969677884

SN - 1523-7060

VL - 18

SP - 2280

EP - 2283

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides

Abstract

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