Catalytic 1,2-Dicyanation of Alkynes by Palladium(II) under Aerobic Conditions

被引：27

作者：

Arai, Shigeru ^{[1
]}

Sato, Takashi ^{[1
]}

Nishida, Atsushi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 11-12期

关键词：

alkynes; cyanation; oxygen; palladium; CARBON TRIPLE BONDS; TRIMETHYLSILYL CYANIDE; STEREOSELECTIVE SYNTHESIS; TERMINAL ACETYLENES; OXIDATIVE ADDITION; C-C; NICKEL; ARYLCYANATION; ARYLACETYLENES; CYANATION;

D O I：

10.1002/adsc.200900334

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A stereoselective 1,2-dicyanation of various alkynes in the presence of trimethylsilyl cyanide (TMSCN) by palladium(II) catalysis under aerobic conditions is investigated. This reaction includes two cyanation pathways, syn- and anti-cyanopalladation to alkynes that are activated by Pd(II). High syn-selectivity was observed in the reaction using terminal alkynes that have bulky substituents at a propargyl position and aliphatic internal alkynes. Furthermore, a dramatic acceleration was observed with substrates having an N-arenesulfonyl functionality at a propargyl position, this indicates that both sulfoxide and carbon-carbon triple bond act as Lewis bases to Pd(II).

引用

页码：1897 / 1904

页数：8

共 50 条

[31] Palladium-catalyzed 1,2-addition of organic halides and terminal alkynes to 7-oxabenzonorbornadiene: An efficient route to polyaromatic hydrocarbons
Kuo, Chun-Jung
Cheng, Shu-Jin
Chang, Shu-Ting
Liu, Charng-Hsing
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) : 485 - 491
[32] Palladium-Catalyzed Carbonylation of Multifunctionalized Substituted Alkynes to Quinolinone Derivatives under Mild Conditions&DAG;
Voronov, Aleksandr
Pancrazzi, Francesco
Constantin, Ana Maria
Maggi, Raimondo
Mancuso, Raffaella
Gabriele, Bartolo
Olivieri, Diego
Carfagna, Carla
Casnati, Alessandro
Rispoli, Francesco
Baldini, Laura
Ca, Nicola Della
CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (23) : 3223 - 3228
[33] X-ray structure of palladium (II) complex and its catalytic activity on Suzuki-Miyaura reaction under mild conditions
Unver, Hakan
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (12) : 7835 - 7846
[34] Development of Silicon Carbide-Supported Palladium Catalysts and Their Application as Semihydrogenation Catalysts for Alkynes under Batch- and Continuous-Flow Conditions
Yamada, Tsuyoshi
Yamamoto, Haruka
Kawai, Kanon
Park, Kwihwan
Aono, Norihiko
Sajiki, Hironao
CATALYSTS, 2022, 12 (10)
[35] Platinum(II) and palladium(II) complexes with 1,2-dihydrobenzoxazol-2-ylidene ligands and molecular structure of trans-bis(1,2-dihydrobenzoxazol-2-ylidene) diiodo palladium
Kernbach, U
Lugger, T
Hahn, FE
Fehlhammer, WP
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 541 (1-2) : 51 - 55
[36] Green synthesis of water-dispersable palladium nanoparticles and their catalytic application in the ligand- and copper-free Sonogashira coupling reaction under aerobic conditions
Nasrollahzadeh, Mahmoud
Maham, Mehdi
Tohidi, Mohammad Mostafa
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 391 : 83 - 87
[37] Phosphine-free palladium catalyzed Suzuki coupling of aryl chlorides in morpholine under aerobic conditions
Guo, Mengping
Zhu, Zhiyong
Huang, Hongwei
Zhang, Qiaochu
CATALYSIS COMMUNICATIONS, 2009, 10 (06) : 865 - 867
[38] Direct Synthesis of 1,2-Diketones by Catalytic Aerobic Oxidative Decarboxylation of 1,3-Diketones with Iodine and Base under Irradiation of Fluorescent Light
Tada, Norihiro
Shomura, Motoki
Nakayama, Hiroki
Miura, Tsuyoshi
Itoh, Akichika
SYNLETT, 2010, (13) : 1979 - 1983
[39] Pd(II) - dppb and syngas catalyze regioselective hydroesterification of terminal alkynes under neutral conditions
El Ali, B
Tijani, J
El-Ghanam, AM
TETRAHEDRON LETTERS, 2001, 42 (12) : 2385 - 2387
[40] Palladium(II)-Catalyzed Cyclization of Unsaturated Hydroperoxides for the Synthesis of 1,2-Dioxanes
Harris, Jason R.
Waetzig, Shelli R.
Woerpel, K. A.
ORGANIC LETTERS, 2009, 11 (15) : 3290 - 3293

← 1 2 3 4 5 →