Palladium-Catalyzed Domino Dehydrogenation/Heck-Type Reactions of Carbonyl Compounds

被引：27

作者：

Le Bras, Jean ^{[1
]}

Muzart, Jacques ^{[1
]}

机构：

[1] Univ Reims, CNRS, Inst Chim Mol Reims, UMR 7312, BP 1039, F-51687 Reims 2, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 13期

基金：

美国国家科学基金会;

关键词：

carbonyl compounds; C-H bond activation; dehydrogenation; domino reaction; Heck reaction; palladium; BETA-KETO-ESTERS; INTRAMOLECULAR HECK REACTION; AUTO-TANDEM CATALYSIS; C-H OLEFINATION; EFFICIENT SYNTHESIS; MOLECULAR-OXYGEN; DIRECT ARYLATION; ALPHA-ARYLATION; ARYL HALIDES; DECARBOXYLATIVE PALLADATION;

D O I：

10.1002/adsc.201800258

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

This review covers those domino reactions that involve, at least, both palladium-catalyzed dehydrogenation of carbonyl compounds and Heck-type reactions. While the former occurs under Pd(II) catalysis, a Pd(0) or Pd(II) catalyst is required for the latter, depending on the nature of the (hetero)arylating agent, ArX or ArH, respectively. Regeneration of the Pd(II) species is assumed to proceed by either an oxidant or the aryl halide. Proposed mechanisms are described with, in some cases, personal comments.

引用

页码：2411 / 2428

页数：18

共 50 条

[41] Comparing nickel- and palladium-catalyzed Heck reactions
Lin, BL
Liu, L
Fu, Y
Luo, SW
Chen, Q
Guo, QX
ORGANOMETALLICS, 2004, 23 (09) : 2114 - 2123
[42] HECK-TYPE REACTIONS IN WATER
JEFFERY, T
TETRAHEDRON LETTERS, 1994, 35 (19) : 3051 - 3054
[43] Palladium-catalyzed Mizoroki-Heck-type reactions using telluronium salts
Hirabayashi, K
Nara, Y
Shimizu, T
Kamigata, N
CHEMISTRY LETTERS, 2004, 33 (10) : 1280 - 1281
[44] Palladium-catalyzed δ-selective reductive Heck reaction of alkenyl carbonyl compounds with aryl iodides and bromides
Li, Yang
Gong, Jun-Fang
Song, Mao-Ping
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (16) : 2216 - 2223
[45] Palladium-catalyzed hydrolysis of dimethylhydrazone to carbonyl compounds
Mino, T
Hirota, T
Yamashita, M
SYNLETT, 1996, (10) : 999 - &
[46] Palladium-Catalyzed Selective Reduction of Carbonyl Compounds
Sarkar, Nabin
Mahato, Mamata
Nembenna, Sharanappa
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (23) : 2295 - 2301
[47] Palladium-Catalyzed Hydrolysis of Dimethylhydrazone to Carbonyl Compounds
Synlett, 10 (999):
[48] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles
Culkin, DA
Hartwig, JF
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 234 - 245
[49] Palladium-catalyzed deprotection of hydrazones to carbonyl compounds
Mino, T
Hirota, T
Fujita, N
Yamashita, M
SYNTHESIS-STUTTGART, 1999, (12): : 2024 - 2026
[50] Transition-Metal-Catalyzed Alkyl Heck-Type Reactions
Kurandina, Daria
Chuentragool, Padon
Gevorgyan, Vladimir
SYNTHESIS-STUTTGART, 2019, 51 (05): : 985 - 1005

← 1 2 3 4 5 →