Cobalt-Catalyzed Cross-Dehydrogenative C(sp2)-C(sp3) Coupling of Oxazole/Thiazole with Ether or Cycloalkane

被引：31

作者：

Wang, Xiaojiao ^{[1
]}

Lei, Bowen ^{[1
]}

Ma, Lifang ^{[1
]}

Zhu, Lisi ^{[1
]}

Zhang, Xinyue ^{[1
]}

Zuo, Hao ^{[1
]}

Zhuang, Dailin ^{[1
]}

Li, Ziyuan ^{[1
]}

机构：

[1] Sichuan Univ, Sch Chem Engn, Dept Pharmaceut & Biol Engn, 24 South Sect 1,Yihuan Rd, Chengdu 610065, Sichuan, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2017年 / 12卷 / 21期

关键词：

C-H bond cleavage; cross-coupling reactions; cycloalkylation; oxazoles; oxyalkylation; METAL-FREE CONDITIONS; DIRECT ALPHA-ARYLATION; C-H FUNCTIONALIZATION; C(SP(3))-H BONDS; PEPTIDE ANTIBIOTICS; INDOLE-DERIVATIVES; LITHISTID SPONGE; CYCLIC ETHERS; N-OXIDES; AZOLES;

D O I：

10.1002/asia.201701258

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct C5-alkylation of oxazole/thiazole with ether or cycloalkane has been achieved through a cobalt-catalyzed cross-dehydrogenative coupling (CDC) process in moderate to good yields. This transformation represents the first C(sp(2))-C(sp(3)) cross-coupling at the C5-position of the oxazole/thiazole via double C-H bond cleavages. Various functional groups on oxazole/thiazole substrates, as well as water and air, are well-tolerated with this concise and practical protocol, constituting straightforward access to heterocycles with great medicinal significance. A preliminary mechanism involving a radical process has also been proposed.

引用

页码：2799 / 2803

页数：5

共 50 条

[1] Cobalt-Catalyzed Cross-Dehydrogenative Coupling Reaction between Unactivated C(sp2)-H and C(sp3)-H Bonds
Li, Qun
Hu, Weipeng
Hu, Renjian
Lu, Hongjian
Li, Guigen
ORGANIC LETTERS, 2017, 19 (17) : 4676 - 4679
[2] Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling
Ludwig, Jacob R.
Simmons, Eric M.
Wisniewski, Steven R.
Chirik, Paul J.
ORGANIC LETTERS, 2021, 23 (03) : 625 - 630
[3] Cobalt-Catalyzed Green Cross-Dehydrogenative C(sp2)-H/P-H Coupling Reactions
Mikhail Khrizanforov
Sofia Strekalova
Vera Khrizanforova
Alexey Dobrynin
Kirill Kholin
Tatyana Gryaznova
Valeriya Grinenko
Aidar Gubaidullin
M. K. Kadirov
Yulia Budnikova
Topics in Catalysis, 2018, 61 : 1949 - 1956
[4] Cobalt-Catalyzed Green Cross-Dehydrogenative C(sp2)-H/P-H Coupling Reactions
Khrizanforov, Mikhail
Strekalova, Sofia
Khrizanforova, Vera
Dobrynin, Alexey
Kholin, Kirill
Gryaznova, Tatyana
Grinenko, Valeriya
Gubaidullin, Aidar
Kadirov, M. K.
Budnikova, Yulia
TOPICS IN CATALYSIS, 2018, 61 (18-19) : 1949 - 1956
[5] Cobalt-Catalyzed Switchable Intramolecular Thioenolization/C-H Thiolation and C(sp2)-H/C(sp3)-H Dehydrogenative Coupling
Yao, Zhi
Cai, Zhongliang
Zhen, Long
Jiang, Liqin
ORGANIC LETTERS, 2020, 22 (11) : 4505 - 4510
[6] Iron-catalyzed construction of cyanomethylated thiohydantoins by cross-dehydrogenative C(sp3)-C(sp3) coupling
Morja, Mayur I.
Moradiya, Riddhi B.
Makwana, Bhavik S.
Chikhalia, Kishor H.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (03) : 449 - 457
[7] Visible-Light-Promoted C(sp3)-C(sp2) Cross-Dehydrogenative Coupling of Tertiary Amine with Imidazopyridine
Kibriya, Golam
Bagdi, Avik Kumar
Hajra, Alakananda
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 10619 - 10626
[8] Cobalt-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions of Diarylmanganese Reagents with Secondary Alkyl Iodides
Hofmayer, Maximilian S.
Hammann, Jeffrey M.
Haas, Diana
Knochel, Paul
ORGANIC LETTERS, 2016, 18 (24) : 6456 - 6459
[9] Cobalt-catalyzed C(sp3)-H/C(sp2)-H oxidative coupling between alkanes and benzamides
Li, Shuangjie
Wang, Bao
Dong, Guangyu
Li, Chunpu
Liu, Hong
RSC ADVANCES, 2018, 8 (24) : 13454 - 13458
[10] Visible-Light-Promoted Radical Cross-Dehydrogenative Coupling of C(sp3)-H/C(sp3)-H and C(sp3)-H/C(sp2)-H via Intermolecular HAT
Xie, Xinpeng
Qiao, Kaikai
Shao, Bing-ru
Jiang, Wenfeng
Shi, Lei
ORGANIC LETTERS, 2023, 25 (23) : 4264 - 4269

← 1 2 3 4 5 →