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题名: Rh(III)- and Ir(III)-Catalyzed C-H Alkynylation of Arenes under Chelation Assistance
作者: Xie, Fang1;  Qi, Zisong1;  Yu, Songjie1;  Li, Xingwei1
刊名: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
发表日期: 2014-03-26
DOI: 10.1021/ja501910e
卷: 136, 期:12, 页:4780-4787
收录类别: SCI ;  IC
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: An efficient Rh(III)- and Ir(III)-catalyzed, chelation-assisted C H alkynylation of a broad scope of (hetero)arenes has been developed using hypervalent iodine-alkyne reagents. Heterocycles, N-methoxy imines, azomethine;mines, secondary carboxamides, azo compounds, N-nitrosoamines, and nitrones are viable directing groups to entail ortho C H alkynylation. The reaction proceeded under mild conditions and with controllable mono- and dialkynylation selectivity when both mono- and dialkynylation was observed. Rh(III) and Ir(III) catalysts exhibited complementary substrate scope in this reaction. The synthetic applications of the coupled products have been demonstrated in subsequent derivatization reactions. Some mechanistic studies have been conducted, and two Rh(III) complexes have been established as key reaction intermediates. The current C-H alkynylation system complements those previously reported under gold or palladium catalysis using hypervalent iodine reagents.
关键词[WOS]: CATALYZED DIRECT ALKYNYLATION ;  CARBOXYLIC-ACID DERIVATIVES ;  OXIDIZING DIRECTING GROUP ;  N BOND FORMATION ;  AZOMETHINE YLIDES ;  TERMINAL ALKYNES ;  ISOQUINOLONE SYNTHESIS ;  C(SP(3))-H BONDS ;  ROOM-TEMPERATURE ;  NATURAL-PRODUCTS
语种: 英语
WOS记录号: WOS:000333551800048
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/143209
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

Recommended Citation:
Xie, Fang,Qi, Zisong,Yu, Songjie,et al. Rh(III)- and Ir(III)-Catalyzed C-H Alkynylation of Arenes under Chelation Assistance[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2014,136(12):4780-4787.
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