Dihalooxygenation of Alkynes and Alkynols: Preparation of 2,2-Dihaloketones and gem-Dihalolactols

被引：6

作者：

Chaisan, Nattawadee ^{[1
]}

Ruengsangtongkul, Sureeporn ^{[2
]}

Thongsornkleeb, Charnsak ^{[1
,2
]}

Tummatorn, Jumreang ^{[1
,2
]}

Ruchirawat, Somsak ^{[1
,2
]}

机构：

[1] Chulabhorn Grad Inst, MHESI, Program Chem Biol, Ctr Excellence Environm Hlth & Toxicol EHT,OPS, 54 Kamphaeng Phet 6, Bangkok 10210, Thailand

[2] Chulabhorn Res Inst, Lab Med Chem, 54 Kamphaeng Phet 6, Bangkok 10210, Thailand

来源：

SYNLETT | 2022年 / 33卷 / 14期

关键词：

dihaloketones; dihalolactols; alkynes; alkynols; halogenation; N-HALOSUCCINIMIDES; HALOGENATION; CATALYST; KETONES;

D O I：

10.1055/a-1774-7077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and convenient method for the synthesis of 2,2-dihaloketones and gem-dihalolactols has been developed. For the synthesis of 2,2-dihaloketones, alkynes were employed as substrates to react with halogenating agents, Cl-2 or CIBr, that were generated in situ from aqueous HCl and NCS or NBS, respectively. On the other hand, gem-dihalolactols could be prepared from alkynol substrates by using the same reaction conditions. This method could be applied to a broad range of substrates to give the corresponding products in low to good yields.

引用

页码：1426 / 1430

页数：5

共 30 条

[11] A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones [J].

Iacono, Carmelo E. ;

Stephens, Thomas C. ;

Rajan, Teena S. ;

Pattison, Graham .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (06) :2036-2040

[12] Isomerizable (E/Z)-alkynyl-O-methyl oximes employing TMSCl-NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles [J].

Kaewsri, Wilailak ;

Thongsornkleeb, Charnsak ;

Tummatorn, Jumreang ;

Ruchirawat, Somsak .

RSC ADVANCES, 2016, 6 (54) :48666-48675

[13] Visible-light-promoted oxidative halogenation of alkynes [J].

Li, Yiming ;

Mou, Tao ;

Lu, Lingling ;

Jiang, Xuefeng .

CHEMICAL COMMUNICATIONS, 2019, 55 (95) :14299-14302

[14] Selective 1,2-dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides [J].

Liu, Jinhua ;

Li, Wenjuan ;

Wang, Chao ;

Li, Yao ;

Li, Zhiping .

TETRAHEDRON LETTERS, 2011, 52 (33) :4320-4323

[15] Practical and Metal-Free Electrophilic Aromatic Halogenation by Interhalogen Compounds Generated In Situ from N-Halosuccinimide and Catalytic TMSCl [J].

Maibunkaew, Tapanee ;

Thongsornkleeb, Charnsak ;

Tummatorn, Jumreang ;

Bunrit, Anon ;

Ruchirawat, Somsak .

SYNLETT, 2014, 25 (12) :1769-1775

[16] MOLECULAR-REARRANGEMENTS .13. KINETICS AND MECHANISM OF REARRANGEMENTS OF SOME RING-SUBSTITUTED ALPHA-CHLOROSTYRENE OXIDES AND TRANS-BETA-CHLOROSTYRENE OXIDES [J].

MCDONALD, RN ;

COUSINS, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15) :2976-2984

[17] Electrochemical Oxidative Oxydihalogenation of Alkynes for the Synthesis of α,α-Dihaloketones [J].

Meng, Xiangtai ;

Zhang, Yu ;

Luo, Jinyue ;

Wang, Fei ;

Cao, Xiaoji ;

Huang, Shenlin .

ORGANIC LETTERS, 2020, 22 (03) :1169-1174

[18] Metal-Free Synthesis of 4-Chloroisocournarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters [J].

Norseeda, Krissada ;

Chaisan, Nattawadee ;

Thongsornkleeb, Charnsak ;

Tummatorn, Jumreang ;

Ruchirawat, Somsak .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (24) :16222-16236

[19] 1-Amino-4,5-8-naphthalenetricarboxylic acid-1,8-lactam-4,5-imide-containing macrocycles:: synthesis, molecular modelling and polymerization [J].

Ponce, P ;

Fomina, L ;

García, P ;

Fomine, S .

POLYMER INTERNATIONAL, 2003, 52 (09) :1454-1461

[20] Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions [J].

Pravst, Igor ;

Zupan, Marko ;

Stavber, Stojan .

TETRAHEDRON, 2008, 64 (22) :5191-5199

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