Synthesis 2020; 52(08): 1223-1230
DOI: 10.1055/s-0039-1690737
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

Yuzhong Yang
,
Liwei Zhou
,
Xiumei Yang
,
Xiai Luo
,
Guobo Deng
,
Yuan Yang
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, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   eMail: yuanyang@hunnu.edu.cn   eMail: yliang@hunnu.edu.cn
,
Yun Liang
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, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   eMail: yuanyang@hunnu.edu.cn   eMail: yliang@hunnu.edu.cn
› Institutsangaben
This work was supported by the National Natural Science Foundation of China (21572051, 21602057, 21901071, and 21971061), Scientific Research Foundation of Hunan Provincial Education Department (18A002), and Science and Technology Planning Project of Hunan Province (2018TP1017).
Weitere Informationen

Publikationsverlauf

Received: 28. August 2019

Accepted after revision: 16. Oktober 2019

Publikationsdatum:
29. Oktober 2019 (online)


Published as part of the Special Topic Domino C–H Functionalization Reaction/Cascade Catalysis

Abstract

A new palladium-catalyzed domino alkyne insertion/C–H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

Supporting Information

 
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