Pd-Catalyzed Allylic Substitution Using Nucleophilic Amines: Access to Functionalized Mono- and Bis-N-Allyl Synthons

被引：0

作者：

Gao, Fengyun ^{[1
,2
]}

Ghorai, Debasish ^{[1
]}

Benet-Buchholz, Jordi ^{[1
]}

Kleij, Arjan W. ^{[1
,3
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain

[2] Univ Rovira I Virgili, Dept Quim Fis & Inorgan, 43007 Tarragona, Spain

[3] Catalan Inst Res & Adv Studies ICREA, Pg Lluis Co 23, Barcelona 08010, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 22期

关键词：

Allylic Substitution; Homogeneous Catalysis; Nucleophilic Amines; Palladium; Synthetic Chemistry; KINETIC ASYMMETRIC TRANSFORMATIONS; VINYLETHYLENE CARBONATES; ENANTIOSELECTIVE CONSTRUCTION; ALLENYLETHYLENE CARBONATES; PD-2(DBA)(3); ANNULATION; REACTIVITY; SCAFFOLDS; ALKENES; WATER;

D O I：

10.1002/adsc.202400685

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We here report a catalytic strategy to enable the decarboxylative allylic amination of vinyl cyclic carbonates using various aliphatic and nucleophilic amines. The use of a protic medium and chelating diphosphine ligands are the main drivers towards chemoselective allylic amine formation, thereby minimizing undesired ligand-driven complex speciation and aminolysis of the involved substrate. This improved approach amplifies the repertoire of allylic amine synthons that can be prepared from a variety of substrate combinations.

引用

页码：4709 / 4714

页数：6

共 50 条

[31] Heterogeneous Pd-catalyzed asymmetric allylic substitution using resin-supported trost-type bisphosphane ligands
Song, CE
Yang, JW
Roh, EJ
Lee, SG
Ahn, JH
Han, HY
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (20) : 3852 - 3854
[32] Selective Mono- and Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions
Jayaraman, Aravindan
Lee, Sunwoo
ORGANIC LETTERS, 2019, 21 (19) : 7923 - 7927
[33] Direct Access to α,β-Alkynylamides via Pd-Catalyzed Carbonylation of Terminal Alkynes with Amines Using Chloroform as the CO Surrogate
Rathod, Gajanan K. K.
Jain, Rahul
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7219 - 7227
[34] Pd-Catalyzed Site-Selective Mono-allylic Substitution and Bis-arylation by Directed Allylic C-H Activation: Synthesis of anti-γ-(Aryl,Styryl)-β-hydroxy Acids and Highly Substituted Tetrahydrofurans
Nallasivam, Jothi L.
Fernandes, Rodney A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (40) : 13238 - 13245
[35] Pd-catalyzed cross-coupling of Baylis-Hillman acetate adducts with bis(pinacolato)diboron: An efficient route to functionalized allyl borates
Kabalka, GW
Venkataiah, B
Dong, G
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17): : 5807 - 5809
[36] Enantioselective Pd-Catalyzed Allylic Substitution using Phosphite-Oxazoline PHOX-Based Ligands containing a Methylene Linker
de la Cruz-Sanchez, Pol
Biosca, Maria
Magre, Marc
Faiges, Jorge
Margalef, Jessica
Pamies, Oscar
Dieguez, Montserrat
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2022, 2022 (10)
[37] Construction of chiral quaternary carbon centers by Pd-catalyzed asymmetric allylic substitution with P,N-1,1′-ferrocene ligands
Hou, XL
Sun, N
ORGANIC LETTERS, 2004, 6 (24) : 4399 - 4401
[38] Synthesis of 1-[bis(trifluoromethyl)phosphine]-1′-oxazolinylferrocene ligands and their application in regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates
Lai, Zeng-Wei
Yang, Rong-Fei
Ye, Ke-Yin
Sun, Hongbin
You, Shu-Li
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1261 - 1266
[39] Ligand tuning in asymmetric catalysis: Mono- and bis-phospholanes for a prototypical Pd-catalyzed asymmetric allylation reaction (vol 2, pg 199, 2000)
Yan, YY
RajanBabu, TV
ORGANIC LETTERS, 2000, 2 (04) : 569 - 569
[40] Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
Rao, Maddali L. N.
Kumar, Abhijeet
TETRAHEDRON, 2014, 70 (39) : 6995 - 7005

← 1 2 3 4 5 →