Photoinduced Transition-Metal-Free Cross-Coupling of Aryl Halides with H-Phosphonates

被引：92

作者：

Zeng, Huiying ^{[1
]}

Dou, Qian ^{[1
]}

Li, Chao-Jun ^{[1
,2
,3
]}

机构：

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

[2] McGill Univ, Dept Chem, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada

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

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 05期

关键词：

CATALYST-FREE; ROOM-TEMPERATURE; DIRECT ARYLATION; P-ARYLATION; BUTOXIDE; TRIFLUOROMETHYLATION; DIPHENYLPHOSPHINE; BONDS; OXIDE;

D O I：

10.1021/acs.orglett.8b04081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photoinduced transition-metal- and photosensitizer-free cross coupling of aryl halides (including Ar-Cl, Ar-Br, and Ar-I) with H-phosphonates (including dialkyl phosphonates and diarylphosphine oxides) is reported. Various functional groups were tolerated, including ester, methoxy, dimethoxy, alkyl, phenyl, trifluoromethyl, and heterocyclic compounds. This simple and green strategy provides a practical pathway to synthesize arylphosphine oxides.

引用

页码：1301 / 1305

页数：5

共 50 条

[1] Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes
He, Qing
Wang, Liwen
Liang, Yong
Zhang, Zunting
Wnuk, Stanislaw F.
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9422 - 9427
[2] Synthesis of α-aryl ketones through transition-metal-free cross-coupling
Nature Synthesis, 2023, 2 : 1138 - 1139
[3] Transition-metal-free Coupling Reactions of Aryl Halides
Shirakawa, Eiji
Hayashi, Tamio
CHEMISTRY LETTERS, 2012, 41 (02) : 130 - 134
[4] Synthesis of α-aryl ketones through transition-metal-free cross-coupling
Li, Xue
Song, Qiuling
NATURE SYNTHESIS, 2023, 2 (12): : 1138 - 1139
[5] Alkoxy base-mediated transition-metal-free cross-coupling reactions of benzene with aryl halides
Liu, Wei
Xu, Lige
Bi, Yanlan
RSC ADVANCES, 2014, 4 (85): : 44943 - 44947
[6] Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes (vol 81, pg 9422, 2016)
He, Qing
Wang, Wenli
Liang, Yong
Zhang, Zunting
Wnuk, Stanislaw F.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7892 - 7892
[7] Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates
Jin, Fengli
Han, Wei
CHEMICAL COMMUNICATIONS, 2015, 51 (44) : 9133 - 9136
[8] Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents
Yang, Bo
Wang, Zhong-Xia
ORGANIC LETTERS, 2017, 19 (22) : 6220 - 6223
[9] Transition-Metal-Free Alkoxycarbonylation of Aryl Halides
Zhang, Hua
Shi, Renyi
Ding, Anxing
Lu, Lijun
Chen, Borui
Lei, Aiwen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (50) : 12542 - 12545
[10] Transition-metal-free cross-coupling reaction of benzylic halides with arylboronic acids leading to diarylmethanes
Ueda, Mitsuhiro
Nakakoji, Daiki
Kuwahara, Yuki
Nishimura, Kota
Ryu, Ilhyong
TETRAHEDRON LETTERS, 2016, 57 (37) : 4142 - 4144

← 1 2 3 4 5 →