Synthesis 2013; 45(22): 3137-3146
DOI: 10.1055/s-0033-1338534
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-Alkynyltetrahydrofuran Derivatives from Tetrahydrofuran and Alkynyl Bromides

Yuan Yang
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   Email: yliang@hunnu.edu.cn
,
Hui Huang
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   Email: yliang@hunnu.edu.cn
,
Xiaoyun Zhang
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   Email: yliang@hunnu.edu.cn
,
Weilan Zeng
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   Email: yliang@hunnu.edu.cn
,
Yun Liang*
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   Email: yliang@hunnu.edu.cn
b   Beijing National Laboratory for Molecular Sciences, Beijing, 100871, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 24 June 2013

Accepted after revision: 29 August 2013

Publication Date:
25 September 2013 (online)


Abstract

An efficient and general method for the synthesis of 2-alkynyltetrahydrofuran was developed. The regioselective functionalization of the C(sp3)–H bond adjacent to an oxygen atom with various alkynyl bromides has been achieved under transition-metal-free reaction conditions. Sodium fluoride was found, for the first time, to promote the efficient functionalization process remarkably. Moreover, 1,2-dibromostyrenes were also found to be effective in this method forming 2-alkenyltetrahydrofurans.

Supporting Information

 
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