Expedient Synthesis of Dihaloalkenynes via Pd-Catalyzed Haloalkynylation Reaction

被引：2

作者：

Ji, Xiaoliang ^{[1
,2
]}

Peng, Xin ^{[1
]}

Hong, Huanliang ^{[1
]}

Xu, Yanghao ^{[1
]}

Nie, Jinli ^{[1
]}

Chen, Lu ^{[1
]}

Mo, Zongwen ^{[1
]}

Li, Yibiao ^{[1
]}

Jiang, Huanfeng ^{[2
]}

机构：

[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529090, Guangdong, Peoples R China

[2] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510641, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 26期

关键词：

dihaloalkane; haloalkyne; haloalkynylation; halopalladation; palladium; C DOUBLE-BONDS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; ALKYNES; BROMOALKYNYLATION; ALKYNYLATION;

D O I：

10.1002/chem.202300068

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, the Pd-II-catalyzed construction of functionalized dihaloalkenynes from haloalkynes via a self-haloalkynylation reaction, without specialized ligands or oxidizing additives, is reported. The method tolerates a diverse range of haloalkynes, including electron-donating and electron-withdrawing functional groups, such as macrocyclic alkynols, spiro-oxy ring alkynols, and even carbazole-containing, pyrrolidine-2,5-dione-containing and silyl-protected bromoalkynes. Using an opposite lithium halide (LiX) to the haloalkyne starting material, remarkably high regio- and stereoselectivity of the haloalkynylation reaction is possible, yielding 1-bromo-2-chloroalkenyne or 2-bromo-1-chloroalkenyne products as desired.

引用

页数：7

共 50 条

[1] Synthesis of Cyclic Sulfonamides via Pd-Catalyzed Intramolecular Coupling Reaction: An Expedient Approach to Polycyclic Sultams
Majumdar, K. C.
Mondal, Shovan
De, Nirupam
SYNLETT, 2008, (18) : 2851 - 2855
[2] Synthesis of Biquinolines via a Pd-Catalyzed Borylation Reaction
Gupta, Shiv S.
Sharma, Krishna K.
Prajapati, Manoj
Rathod, Gajanan K.
Jain, Rahul
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) : 1581 - 1584
[3] Convergent synthesis of (+)-xestodecalactone A via a Pd-catalyzed α-arylation reaction
De Joarder, Dripta
Jennings, Michael P.
TETRAHEDRON LETTERS, 2013, 54 (30) : 3990 - 3992
[4] Synthesis of Cyclic Peptidomimetics via a Pd-Catalyzed Macroamination Reaction
Hopkins, Brett A.
Smith, Graham F.
Sciammetta, Nunzio
ORGANIC LETTERS, 2016, 18 (16) : 4072 - 4075
[5] Expedient synthesis of 3-substituted cycloalkanones via a Pd-catalyzed decarboxylative protonation protocol
Kim, Se Hee
Kim, Eun Sun
Kim, Taek Hyeon
Kim, Jae Nyoung
TETRAHEDRON LETTERS, 2009, 50 (46) : 6256 - 6260
[6] An expedient synthesis of the fibril binding compound FSB via sequential pd-catalyzed coupling reactions
Mantel, Mette Louise H.
Sobjerg, Lina S.
Huynh, Tri H. V.
Ebran, Jean-Philippe
Lindhardt , Anders T.
Nielsen, Niels C.
Skrydstrup, Troels
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09): : 3570 - 3573
[7] Synthesis of (-)-erythrodiene via intramolecular Pd-catalyzed Zn-ene reaction
Oppolzer, W
Flachsmann, F
TETRAHEDRON LETTERS, 1998, 39 (28) : 5019 - 5022
[8] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction
Becht, Jean-Michel
Catala, Cedric
Le Drian, Claude
Wagner, Alain
ORGANIC LETTERS, 2007, 9 (09) : 1781 - 1783
[9] Synthesis of 4-Alkylated Isocoumarins via Pd-Catalyzed α-Arylation Reaction
Plunkett, Shane
DeRatt, Lindsey G.
Kuduk, Scott D.
Balsells, Jaume
ORGANIC LETTERS, 2020, 22 (19) : 7662 - 7666
[10] Synthesis of Enantioenriched Trisubstituted Allenes via Pd-Catalyzed Heck Reaction of Alkynes
Hou, Xuelong
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (06) : 1800 - 1801

← 1 2 3 4 5 →