Palladium-Catalyzed Synthesis of Nucleoside Adducts from Bay- and Fjord-Region Diol Epoxides

Elise Champeil; Padmanava Pradhan; Mahesh K. Lakshman

doi:10.1021/jo070204z

Palladium-Catalyzed Synthesis of Nucleoside Adducts from Bay- and Fjord-Region Diol Epoxides

The Journal of Organic Chemistry ◽

10.1021/jo070204z ◽

2007 ◽

Vol 72 (14) ◽

pp. 5035-5045 ◽

Cited By ~ 14

Author(s):

Elise Champeil ◽

Padmanava Pradhan ◽

Mahesh K. Lakshman

Keyword(s):

Diol Epoxides ◽

Palladium Catalyzed ◽

Nucleoside Adducts

Palladium-Catalyzed Synthesis of Carcinogenic Polycyclic Aromatic Hydrocarbon Epoxide-Nucleoside Adducts: The First Amination of a Chloro Nucleoside1

Organic Letters ◽

10.1021/ol027084w ◽

2003 ◽

Vol 5 (1) ◽

pp. 39-42 ◽

Cited By ~ 16

Author(s):

Mahesh K. Lakshman ◽

Padmaja Gunda

Keyword(s):

Polycyclic Aromatic Hydrocarbon ◽

Aromatic Hydrocarbon ◽

Polycyclic Aromatic ◽

Palladium Catalyzed ◽

Carcinogenic Polycyclic Aromatic Hydrocarbon ◽

Nucleoside Adducts

Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

Organic Chemistry Frontiers ◽

10.1039/d0qo00748j ◽

2020 ◽

Vol 7 (19) ◽

pp. 2938-2943

Author(s):

Yeojin Kim ◽

Kwang Ho Song ◽

Sunwoo Lee

Keyword(s):

Aryl Iodide ◽

Aryl Iodides ◽

Palladium Catalyzed

Aryl sulfonyl hydrazide reacted with aryl iodide in the presence of CO to give the corresponding S-aryl thioesters.

Palladium-catalyzed carbonylative transformation of aryl iodides and sulfonyl chlorides: convenient access to thioesters

Organic Chemistry Frontiers ◽

10.1039/d0qo00158a ◽

2020 ◽

Vol 7 (6) ◽

pp. 885-889 ◽

Cited By ~ 2

Author(s):

Xinxin Qi ◽

Zhi-Peng Bao ◽

Xiao-Feng Wu

Keyword(s):

Sulfonyl Chlorides ◽

Aryl Iodides ◽

Palladium Catalyzed ◽

Convenient Access

A palladium-catalyzed carbonylative transformation of aryl iodides and sulfonyl chlorides to thioesters has been studied.

Palladium-Catalyzed Cross Coupling Reactions of β-Iodo-β,γ-enones with Organozinc Chlorides

The Journal of Organic Chemistry ◽

10.1021/jo974001u ◽

1997 ◽

Vol 62 (6) ◽

pp. 1908-1908

Author(s):

Fen-Tair Luo ◽

Li-Chen Hsieh

Keyword(s):

Cross Coupling ◽

Coupling Reactions ◽

Cross Coupling Reactions ◽

Palladium Catalyzed

Palladium-catalyzed intramolecular zinc-ene reactions

Tetrahedron Letters ◽

10.1016/s0040-4039(00)78390-0 ◽

1994 ◽

Vol 35 (41) ◽

pp. 7939-7942 ◽

Cited By ~ 15

Author(s):

W Oppolzer

Keyword(s):

Ene Reactions ◽

Palladium Catalyzed

Palladium catalyzed cross-coupling reactions of difunctional derivatives Bu3SnArBr. Synthesis of regioregular poly(3-alkylthiophenes) and poly(4-alkyl 2,2'-bithiophenes) with high molecular weights

Journal de Chimie Physique ◽

10.1051/jcp:1998259 ◽

1998 ◽

Vol 95 (6) ◽

pp. 1250-1253 ◽

Cited By ~ 5

Author(s):

J.-P. Lère-Porte ◽

J. J.E. Moreau ◽

C. Torreilles

Keyword(s):

Cross Coupling ◽

Coupling Reactions ◽

Molecular Weights ◽

Cross Coupling Reactions ◽

Regioregular Poly ◽

Palladium Catalyzed

Palladium-Catalyzed Ligand-Controlled Regioselective Acylation

Synfacts ◽

10.1055/s-0037-1612003 ◽

2019 ◽

Vol 15 (02) ◽

pp. 0158

Keyword(s):

Regioselective Acylation ◽

Palladium Catalyzed

Synthesis of Allenyl Ketones by the Palladium-Catalyzed Carbonylation of 2-Alkynyl Carbonates in the Presence of Soft Carbon Nucleophiles

Synlett ◽

10.1055/s-1991-20842 ◽

1991 ◽

Vol 1991 (09) ◽

pp. 697-698 ◽

Cited By ~ 1

Author(s):

Tadakatsu Mandai ◽

Hiroaki Kunitomi ◽

Kiyoto Higashi ◽

Mikio Kawada ◽

Jiro Tsuji

Keyword(s):

Carbon Nucleophiles ◽

Palladium Catalyzed ◽

Soft Carbon

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

10.26434/chemrxiv.11857857 ◽

2020 ◽

Author(s):

Kiron Kumar Ghosh ◽

Alexander Uttry ◽

Francesca Ghiringhelli ◽

Arup Mondal ◽

Manuel van Gemmeren

Keyword(s):

Reaction Mechanism ◽

Carboxylic Acids ◽

Michael Addition ◽

Kinetic Studies ◽

Wide Range ◽

Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

10.26434/chemrxiv.12034743 ◽

2020 ◽

Author(s):

Aleksandra Balliu ◽

Aaltje Roelofje Femmigje Strijker ◽

Michael Oschmann ◽

Monireh Pourghasemi Lati ◽

Oscar Verho

Keyword(s):

Carboxylic Acid ◽

Building Blocks ◽

Wide Range ◽

Palladium Catalyzed ◽

Directing Group ◽

High Yields ◽

Vinyl Iodides ◽

Initial Results

In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both cis- and trans-configured carboxylic acid building blocks from the C–H alkenylation products.