Defluorinative C(sp3)-P Bond Construction for the Synthesis of Phosphorylation gem-Difluoroalkenes under Catalyst- and Oxidant-Free Conditions

被引：22

作者：

Li, Congyu ^{[1
]}

Yuan, Jing-Mei ^{[2
]}

Chen, Wenqiang ^{[1
]}

He, Yimiao ^{[1
]}

Huang, Jun ^{[1
]}

Huang, Yanmin ^{[1
]}

Xiao, Qi ^{[1
]}

Sheng, Jiarong ^{[1
]}

Huang, Chusheng ^{[1
]}

机构：

[1] Nanning Normal Univ, Guangxi Key Lab Nat Polymer Chem & Phys, 175 East Mingxiu Rd, Nanning 530001, Guangxi, Peoples R China

[2] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, 15 Yucai Rd, Guilin 541004, Guangxi, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2019年 / 14卷 / 15期

基金：

中国国家自然科学基金;

关键词：

C(sp(3))-P bond; gem-difluoroalkenes; phosphorylation; S(N)2 ' process; alpha-trifluoromethyl alkenes; DEHYDROGENATIVE-COUPLING REACTIONS; OXIDATIVE C-C; TRIFLUOROMETHYL ALKENES; PHOSPHINE OXIDES; EFFICIENT; CASCADE; PHOSPHONOPEPTIDES; DIPHENYLPHOSPHINE; ALKYLATION; STYRENES;

D O I：

10.1002/asia.201900533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Defluorinative C(sp(3))-P bond formation of alpha-trifluoromethyl alkenes with phosphine oxides or phosphonates have been achieved under catalyst- and oxidant-free conditions, giving phosphorylation gem-difluoroalkenes as products. alpha-Trifluoromethyl alkenes bearing various of aryl substituents such as halogen, cyano, ester and heterocyclic groups are available in this transformation. The results of control experiments demonstrated that the mechanism of dehydrogenative/defluorinative cross-coupling reactions was not a radical route, but might be an S(N)2 ' process involving phosphine oxide anion.

引用

页码：2584 / 2587

页数：4

共 47 条

[31] δ and α SP3 C-H bond oxidation of Sulfonamides with PhI(OAc)2/I2 under metal-free conditions
Fan, Renhua
Pu, Dongming
Wen, Fengqi
Wu, Jie
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (23): : 8994 - 8997
[32] Intermolecular Oxidative C-N Bond Formation under Metal-Free Conditions: Control of Chemoselectivity between Aryl sp2 and Benzylic sp3 C-H Bond Imidation
Kim, Hyun Jin
Kim, Jiyu
Cho, Seung Hwan
Chang, Sukbok
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16382 - 16385
[33] Visible-Light-Induced C (sp3)-H Functionalization of Tosylhydrazones: Synthesis of Polysubstituted Pyrroles under Metal-Free Conditions
Reddy, N. Naresh Kumar
Rawat, Deepa
Adimurthy, Subbarayappa
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16): : 9412 - 9421
[34] DDQ-Catalyzed Direct C(sp3)-H Amination of Alkylheteroarenes: Synthesis of Biheteroarenes under Aerobic and Metal-Free Conditions
Song, Chunlan
Dong, Xin
Yi, Hong
Chiang, Chien-Wei
Lei, Aiwen
ACS CATALYSIS, 2018, 8 (03): : 2195 - 2199
[35] Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp3)-O Bond Formation Tandem Reaction
Zhang, Mingliang
Zhao, Pin
Liu, Qilv
Liu, Xinlei
Hu, Jingya
Wu, Dongqing
Liu, Lantao
MOLECULES, 2023, 28 (14):
[36] Visible-light-induced C(sp3)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions
Akula, Pavan Sudheer
Hong, Bor-Cherng
Lee, Gene-Hsiang
RSC ADVANCES, 2018, 8 (35): : 19580 - 19584
[37] Microwave assisted catalyst-free synthesis of azaarene-substituted 3-hydroxy-2-oxindoles by the functionalization of sp3 C-H bond in methyl pyridine
Meshram, H. M.
Rao, N. Nageswara
Rao, L. Chandrasekhara
Kumar, N. Satish
TETRAHEDRON LETTERS, 2012, 53 (31) : 3963 - 3966
[38] Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp3C-P bonds
Li, Qiang
Zhao, Chang-Qiu
Chen, Tieqiao
Han, Li-Biao
RSC ADVANCES, 2022, 12 (29) : 18441 - 18444
[39] Photoredox and cobalt co-catalyzed C(sp2)-H functionalization/C-O bond formation for synthesis of lactones under oxidant- and acceptor-free conditions
Zhang, Muliang
Ruzi, Rehanguli
Li, Nan
Xie, Jin
Zhu, Chengjian
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (05): : 749 - 752
[40] Electrochemical oxidative synthesis of 2-benzoylquinazolin-4(3H)-one via C(sp3)-H amination under metal-free conditions
Hu, Yongzhi
Ma, Xinhua
Hou, Huiqing
Sun, Weiming
Tu, Shuqing
Wu, Mei
Lin, Rongkun
Xu, Xiuzhi
Ke, Fang
CATALYSIS SCIENCE & TECHNOLOGY, 2021, 11 (19) : 6374 - 6379

← 1 2 3 4 5 →