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Synlett 2019; 30(02): 124-128
DOI: 10.1055/s-0037-1610335
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© Georg Thieme Verlag Stuttgart · New York

Manganese(I)-Catalyzed Selective Functionalization of Alkynes

Zhongfei Yan
,
Chengjian Zhu
,
Jin Xie*
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P. R. of China   Email: xie@nju.edu.cn
› Author AffiliationsWe gratefully acknowledge financial support from the National Natural Science Foundation of China (21702098, 21672099 and 21732003), the Fundamental Research Funds for the Central Universities (No. 020514380158, 020514380131), the ‘1000-Youth Talents Plan’ and the program A for Outstanding PhD candidate of Nanjing University (201802A018).
Further Information

Publication History

Received: 16 October 2018

Accepted after revision: 25 October 2018

Publication Date:
30 November 2018 (online)

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Abstract

Mn(I)-catalyzed selective functionalization of alkynes permits the convenient synthesis of substituted alkenes with high step and atom economies. Although the insertion of five-membered chelated manganacycle intermediates into alkynes has been widely reported, nonchelated Ar–Mn(I) species originating from commercially available arylboronic acids are unprecedented. Our new protocol achieved a challenging hydroarylation of unsymmetrical 1,3-diynes with arylboronic acids with complete regio-, stereo-, and chemoselectivity to give a wide array of trisubstituted conjugated (Z)-enynes in moderate to good yields.

Key words

arylboronic acids - alkynes - C–H activation - manganese catalysis - diynes - enynes
 

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