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将双SO插入1,7-二炔中合成官能化萘并[1,2-]噻吩2,2-二氧化物。

Double SO Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-]thiophene 2,2-dioxides.

作者信息

Wang Ai-Fang, Hao Wen-Juan, Zhu Yi-Long, Li Guigen, Zhou Peng, Tu Shu-Jiang, Jiang Bo

机构信息

School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. China.

Institute of Chemistry & BioMedical Sciences, Nanjing University, Nanjing 210093, P. R. China.

出版信息

ACS Omega. 2018 Feb 5;3(2):1482-1491. doi: 10.1021/acsomega.7b01789. eCollection 2018 Feb 28.

DOI:10.1021/acsomega.7b01789
PMID:31458474
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6641491/
Abstract

A novel metal-free double SO insertion/multicomponent bicyclization cascade of benzene-linked 1,7-diynes has been established by treatment with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) under redox-neutral conditions, providing a range of dual sulfone-containing naphtho[1,2-]thiophene 2,2-dioxides with generally high stereoselectivity. The reaction pathway is proposed to proceed through the sequence of arylsulfonyl-radical-induced 6-exo-dig/5-endo-trig bicyclization, H-abstraction, and diazotization.

摘要

通过在氧化还原中性条件下用四氟硼酸芳基重氮盐和DABCO-双（二氧化硫）处理，建立了一种新型的无金属双SO插入/多组分苯连接的1,7-二炔双环化串联反应，提供了一系列具有普遍高立体选择性的含双砜萘并[1,2-]噻吩2,2-二氧化物。该反应途径被认为是通过芳基磺酰基自由基诱导的6-外向-双环化/5-内向-三环化、氢原子夺取和重氮化的顺序进行的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/5cf997cee230/ao-2017-01789h_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/435f1b488f3b/ao-2017-01789h_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/16cf6bf46247/ao-2017-01789h_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/20aea02c3ae0/ao-2017-01789h_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/0f1fc7cab88c/ao-2017-01789h_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/5cf997cee230/ao-2017-01789h_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/435f1b488f3b/ao-2017-01789h_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/16cf6bf46247/ao-2017-01789h_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/20aea02c3ae0/ao-2017-01789h_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/0f1fc7cab88c/ao-2017-01789h_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/6641491/5cf997cee230/ao-2017-01789h_0006.jpg

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本文引用的文献

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