Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones

被引：8

作者：

Ano, Yusuke ^{[1
,2
]}

Higashino, Masaya ^{[1
]}

Yamada, Yuki ^{[1
]}

Chatani, Naoto ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Ctr Atom & Mol Technol, Suita, Osaka 5650871, Japan

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 23期

关键词：

C-H ACTIVATION; BOND-CLEAVAGE; ORGANIC-SYNTHESIS; COMPLEXES NHC; CONVERSION; N; N-DIMETHYLHYDRAZONES; OXIDATION; ALDEHYDES; N-DIALKYLHYDRAZONES; TRANSFORMATION;

D O I：

10.1039/d2cc00342b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.

引用

页码：3799 / 3802

页数：4

共 53 条

[41] Base- Catalyzed N ∼ N Bond Cleavage of Hydrazones: Synthesis of a- Amino Ketones [J].

Tang, Hai-Tao ;

Zhou, Yun-Bing ;

Zhu, Yu ;

Sun, Hong-Chao ;

Lin, Min ;

Zhan, Zhuang-Ping .

CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (05) :1278-1281

[42] Synthesis of α-phenylselanyl and α-phenylsulfanyl nitriles from aldehyde N,N-dialkylhydrazones [J].

Ternon, M ;

Pannecoucke, X ;

Outurquin, F ;

Paulmier, C .

TETRAHEDRON, 2002, 58 (16) :3275-3279

[43] Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalysed β-X elimination [J].

Tran, Van T. ;

Gurak, John A., Jr. ;

Yang, Kin S. ;

Engle, Keary M. .

NATURE CHEMISTRY, 2018, 10 (11) :1126-1133

[44] Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene) [J].

Viciu, MS ;

Navarro, O ;

Germaneau, RF ;

Kelly, RA ;

Sommer, W ;

Marion, N ;

Stevens, ED ;

Cavallo, L ;

Nolan, SP .

ORGANOMETALLICS, 2004, 23 (07) :1629-1635

[45] Activation and reactivity of (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes in cross-coupling reactions [J].

Viciu, MS ;

Germaneau, RF ;

Navarro-Fernandez, O ;

Stevens, ED ;

Nolan, SP .

ORGANOMETALLICS, 2002, 21 (25) :5470-5472

[46] Pd-Catalyzed Intramolecular C-N Bond Cleavage, 1,4-Migration, sp3 C-H Activation, and Heck Reaction: Four Controllable Diverse Pathways Depending on the Judicious Choice of the Base and Ligand [J].

Wang, Min ;

Zhang, Xiang ;

Zhuang, Yu-Xuan ;

Xu, Yun-He ;

Loh, Teck-Peng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (03) :1341-1347

[47] Reversible Alkene Insertion into the Pd-N Bond of Pd(II)-Sulfonamidates and Implications for Catalytic Amidation Reactions [J].

White, Paul B. ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (46) :18594-18597

[48] Catalytic Enantioselective Cyanation: Recent Advances and Perspectives [J].

Wu, Wen-Biao ;

Yu, Jin-Sheng ;

Zhou, Jian .

ACS CATALYSIS, 2020, 10 (14) :7668-7690

[49] Recent Developments in Radical Cross-Coupling of Redox-Active Cycloketone Oximes [J].

Xiao, Fang ;

Guo, Yu ;

Zeng, Yao-Fu .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (01) :120-143

[50] Iminyl-Radical-Triggered C-C Bond Cleavage of Cycloketone Oxime Derivatives: Generation of Distal Cyano-Substituted Alkyl Radicals and Their Functionalization [J].

Xiao, Tiebo ;

Huang, Hongtai ;

Anand, Devireddy ;

Zhou, Lei .

SYNTHESIS-STUTTGART, 2020, 52 (11) :1585-1601

← 1 2 3 4 5 6 →