Synthesis of δ-Bromo γ,δ-Unsaturated Carbonyl Compounds via Palladium-Catalyzed Bromoalkylation of Alkynoates

被引：37

作者：

Wen, Yanmei ^{[1
,2
]}

Huang, Liangbin ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Chen, Huoji ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

[2] Guangdong Ocean Univ, Coll Sci, Zhanjiang 524088, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 04期

基金：

中国国家自然科学基金;

关键词：

BETA-HETEROATOM ELIMINATION; ALLYL ALCOHOLS; RECONSTITUTIVE CONDENSATION; (Z)-4'-ACETOXY-2'-BUTENYL 2-ALKYNOATES; PALLADIUM(II)-CATALYZED CYCLIZATION; PROPARGYL ALCOHOLS; MOLECULAR-OXYGEN; BOND FORMATION; AQUEOUS-MEDIA; ALKYNES;

D O I：

10.1021/jo202416h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed regio- and stereoselective intermolecular tandem reaction of electron-deficient alkynes, CuBr2, and allylic alcohol to synthesize delta-bromo-gamma,delta-unsaturated carbonyls was developed. A mechanism involving bromopalladation of alkyne, followed by insertion of allylic alcohol and allylic hydrogen shift, is proposed. The shift of allylic hydrogen is the rate-limiting step in this reaction.

引用

页码：2029 / 2034

页数：6

共 50 条

[31] Synthesis of Indolo[2,3-b]quinolines by Palladium-catalyzed Annulation of Unsaturated Isothioureas [J].

Takeda, Hiroshi ;

Ishida, Takayuki ;

Takemoto, Yoshiji .

CHEMISTRY LETTERS, 2009, 38 (08) :772-773

[32] Palladium-catalyzed addition of cyanoboranes to alkynes:: Regio- and stereoselective synthesis of α,β-unsaturated β-boryl nitriles [J].

Suginome, M ;

Yamamoto, A ;

Murakami, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2380-2382

[33] Selective Synthesis of (Z)- and (E)-ß-Fluoro-a,ß-Unsaturated Amides Using Palladium-Catalyzed Aminocarbonylation [J].

Park, Su Hyeon ;

Lee, Sunwoo .

ORGANIC LETTERS, 2023, 25 (37) :6925-6930

[34] Expeditious Synthesis of Highly Substituted Indolizinones via a Palladium-Catalyzed Domino Sequence [J].

Kim, Ikyon ;

Kim, Kyungsun .

ORGANIC LETTERS, 2010, 12 (11) :2500-2503

[35] Synthesis of Indenes and Benzofulvenes via a Palladium-Catalyzed Three-Component Reaction [J].

Abel-Snape, Xavier ;

Wycich, Gina ;

Lautens, Mark .

ACS CATALYSIS, 2022, 12 (06) :3291-3301

[36] Synthesis of Trifluoromethylated Tetrasubstituted Allenes via Palladium-Catalyzed Carbene Transfer Reaction [J].

Pei, Chao ;

Yang, Zhen ;

Koenigs, Rene M. .

ORGANIC LETTERS, 2020, 22 (18) :7300-7304

[37] Synthesis of Cyclic Enones via Direct Palladium-Catalyzed Aerobic Dehydrogenation of Ketones [J].

Diao, Tianning ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14566-14569

[38] Synthesis of Benzo[a]carbazoles via Palladium-Catalyzed Tandem Cyclization of Diarylalkynes with Isocyanides [J].

Wang, Binbin ;

Liu, Shengquan ;

Chen, Ting ;

Jiang, Huanfeng ;

Wu, Wanqing .

ORGANIC LETTERS, 2025, 27 (24) :6316-6323

[39] Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides [J].

Katcher, Matthew H. ;

Doyle, Abigail G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) :17402-17404

[40] Palladium-Catalyzed Direct Synthesis of Organoboronic Acids [J].

Pilarski, Lukasz T. ;

Szabo, Kalman J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) :8230-8232

← 1 2 3 4 5 →