Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex

被引：31

作者：

Pan, Pan ^{[1
]}

Liu, Shihan ^{[2
]}

Lan, Yu ^{[2
,3
]}

Zeng, Huiying ^{[1
]}

Li, Chao-Jun ^{[4
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, 222 Tianshui Rd, Lanzhou 730000, Peoples R China

[2] Chongqing Univ, Sch Chem & Chem Engn, Chongqing Key Lab Theoret & Computat Chem, Chongqing 400030, Peoples R China

[3] Zhengzhou Univ, Coll Chem, Inst Green Catalysis, Zhengzhou 450001, Peoples R China

[4] McGill Univ, FQRNT Ctr Green Chem & Catalysis, Dept Chem, 801 Sherbmoke St West, Montreal, PQ H3A 0B8, Canada

来源：

CHEMICAL SCIENCE | 2022年 / 13卷 / 24期

关键词：

SECONDARY ALKYL BROMIDES; PHOTOINDUCED TRANSITION-METAL; CATALYST-FREE; GRIGNARD-REAGENTS; ZINC REAGENTS; HALIDES; BOND; ALDEHYDES; ACIDS; ARYLATION;

D O I：

10.1039/d2sc01909d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, hydrazones were used as alternatives to organometallic reagents, in the absence of a transition metal or an external photosensitizer, making this cross-coupling mild and green. The protocol was compatible with a variety of functionalities, including methyl, methoxy, trifluoromethyl, halogen, and heteroaromatic rings. Mechanistic investigations showed that the association of the hydrazone anion with aryl halides formed an electron donor-acceptor complex, which when excited with visible light generated an aryl radical via single-electron transfer.

引用

页码：7165 / 7171

页数：7

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