Palladium-Catalyzed Formylation of Aryl Bromides: Elucidation of the Catalytic Cycle of an Industrially Applied Coupling Reaction

2008 ◽  
Vol 130 (46) ◽  
pp. 15549-15563 ◽  
Author(s):  
Alexey G. Sergeev ◽  
Anke Spannenberg ◽  
Matthias Beller
Keyword(s):  
Coupling Reaction ◽  
Catalytic Cycle ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Pd-Catalyzed Cross-Coupling Reaction of Sterically Hindered Vinyl Iodides and Organozinc Reagents. Synthesis of Vitamin D Analogues with an Aromatic Ring Attached at C-17

2002 ◽  
Vol 67 (11) ◽  
pp. 1658-1668 ◽  
Author(s):  
Agnieszka Przezdziecka ◽  
Alicja Kurek-Tyrlik ◽  
Jerzy Wicha
Keyword(s):  
Vitamin D ◽  
Butyl Ester ◽  
Acid Methyl Ester ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Building Blocks ◽  
Vitamin D Analogues ◽  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
Organozinc Reagents

Palladium-catalyzed coupling of steroid 17-iodo-6β-methoxy-3α,5-cyclo-5α-androst-16-ene (4) 17-iodoandrosta-5,16-dien-3β-ol (5), and structurally similar (3aS,7R,7aR)-benzenesulfonyl-3-iodo-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-indene (6) with various arylzinc chlorides, which were generated from aryl bromides 8 [1-bromomethylbenzene (8a), O-(triethylsilyl-2-bromophenyl)propan-2-ol (8b), 2-(4-bromophenyl)propan-2-ol (8c), 4-bromobenzonitrile (8d), 4-bromobenzoic acid methyl ester (8e), 4-bromobenzoic acid tert-butyl ester (8f) and 3-bromopyridine (8g)] via aryllihium derivatives (the Negishi coupling) was examined. The respective cross-coupling products were obtained in good yields for all aryl bromides except of 8c and 8e. Building blocks for synthesis of certain vitamin D analogues have been prepared.

Cationic palladium-catalyzed hydrosilylative cross-coupling of alkynes with alkenes forming 4-silylated-1-butene frameworks

2008 ◽  
Vol 80 (5) ◽  
pp. 1179-1185 ◽  
Author(s):  
Takamitsu Shimamoto ◽  
Motoharu Chimori ◽  
Hiroaki Sogawa ◽  
Yuki Harada ◽  
Masaharu Aoki ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Catalytic Cycle ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Coupling Pattern ◽  
Cationic Palladium

A new hydrosilylative cross-coupling reaction of a variety of alkynes with several alkenes, which is catalyzed by a cationic Pd complex [Pd(η3-C3H5)(cod)]+[PF6]- (cod = 1,5-cyclooctadiene) was studied systematically. The reaction using HSiCl3 as an addend afforded more or less two types of products consisting of four possible derivatives, R1CH=CR2-CHR3-CHR4-SiCl3, which always contained 4-trichlorosilyl-1-butene frameworks, in acceptable combined yields. The coupling pattern was markedly dependent both on the precatalyst in the absence or presence of PPh3 ligand and on the combination of the alkyne and alkene partners employed. A possible catalytic cycle that involves an initial hydropalladation of an alkyne, followed by a facile and specific carbopalladation of an alkene, is proposed. At the same time, the lack of regioselectivity in the latter step is noted.

Palladium-Catalyzed Cross-Coupling Reaction of Aryltriethoxysilanes with Aryl Bromides under Basic Aqueous Conditions

Synthesis ◽  
2001 ◽  
Vol 2001 (15) ◽  
pp. 2231-2233 ◽  
Author(s):  
Miki Murata ◽  
Ryuta Shimazaki ◽  
Shinji Watanabe ◽  
Yuzuru Masuda
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Bromides ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Aqueous Conditions

scholarly journals A facile preparation of 4-aryl-3-[(tert-butyldimethylsilyl)oxymethyl]furans

1991 ◽  
Vol 69 (8) ◽  
pp. 1326-1330 ◽  
Author(s):  
Brian A. Keay ◽  
Jean-Louis J. Bontront
Keyword(s):  
Key Words ◽  
Coupling Reaction ◽  
Aryl Bromides ◽  
Palladium Catalyzed ◽  
Facile Preparation

A series of aryl bromides undergo a palladium-catalyzed coupling reaction with 3-[(tert-butyldimethylsilyl)oxymethyl]-4-(tri-n-butylstannyl)furan to provide 4-aryl-3-[(tert-butyldimethylsilyl)oxymethyl]furans in moderate to good yields. Key words: palladium, cross-couplings, stannanes, 3,4-disubstituted furans.

Palladium-catalyzed coupling reaction of 4-alkylnitrobenzenes with aryl bromides at their benzylic position

1998 ◽  
Vol 39 (26) ◽  
pp. 4673-4676 ◽  
Author(s):  
Jun-Ichi Inoh ◽  
Tetsuya Satoh ◽  
Sommai Pivsa-Art ◽  
Masahiro Miura ◽  
Masakatsu Nomura
Keyword(s):  
Coupling Reaction ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Palladium-Catalyzed Direct C2-Arylation of Benzo[b]thiophenes with Electron-Rich Aryl Halides: Facile Access to Thienoacene Derivatives

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2812-2816 ◽  
Author(s):  
Fumiki Ichioka ◽  
Yuhei Itai ◽  
Yuji Nishii ◽  
Masahiro Miura
Keyword(s):  
Reaction System ◽  
Phenyl Group ◽  
Coupling Reaction ◽  
Direct Coupling ◽  
Aryl Halides ◽  
Facile Synthesis ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Direct coupling reaction of benzo[b]thiophene and electron-rich aryl bromides was achieved under Pd2(dba)3/SPhos catalysis in the presence of NaOt-Bu. The reaction system was applied for the installation of 2-(methylthio)phenyl group onto thiophene-fused polyaromatic molecules, demonstrating facile synthesis of precursors for thienoacene derivatives.

Palladium-Catalyzed Ternary Coupling Reaction Composed of Aryl Bromides, Phenyltributyltin and 1,3-Dioxole

Synlett ◽  
1995 ◽  
Vol 1995 (12) ◽  
pp. 1225-1226 ◽  
Author(s):  
Hiroshi Oda ◽  
Katsuaki Hamataka ◽  
Keigo Fugami ◽  
Masanori Kosugi ◽  
Toshihiko Migita
Keyword(s):  
Coupling Reaction ◽  
Aryl Bromides ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Coupling Reaction of Amino Acids (Esters) with Aryl Bromides and Chlorides.

ChemInform ◽  
2012 ◽  
Vol 43 (30) ◽  
pp. no-no
Author(s):  
Fangfang Ma ◽  
Xiaomin Xie ◽  
Lina Ding ◽  
Jinsheng Gao ◽  
Zhaoguo Zhang
Keyword(s):  
Amino Acids ◽  
Coupling Reaction ◽  
Aryl Bromides ◽  
Palladium Catalyzed
Sign in / Sign up

Export Citation Format

Share Document