Copper Cyanide-Catalyzed Palladium Coupling ofN-tert-Butoxycarbonyl-Protected α-Lithio Amines with Aryl Iodides or Vinyl Iodides

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.

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Palladium-Catalyzed Asymmetric Annulation Between Aryl Iodides and Racemic Epoxides Using a Chiral Norbornene Cocatalyst

10.26434/chemrxiv.6635312 ◽

2018 ◽

Author(s):

Guangbin Dong ◽

Renhe Li

Keyword(s):

Isopropyl Ester ◽

Synthetic Route ◽

Initial Development ◽

Aryl Iodides ◽

Palladium Catalyzed

Herein, we describe our initial development of an asymmetric Pd-catalyzed annulation between aryl iodides and racemic epoxides for synthesis of 2,3-dihydrobenzofurans using a chiral norbornene cocatalyst. A series of enantiopure ester-, amide- and imide-substituted norbornenes have been prepared with a reliable synthetic route. Promising enantioselectivity (42-45% ee) has been observed using the isopropyl ester-substituted norbornene (N1*) and the amide-substituted norbornene (N7*).

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A highly efficient heterogeneous copper-catalysed cascade reaction of aryl iodides with acetamidine hydrochloride leading to primary arylamines_esi

Journal of Chemical Research ◽

10.3184/174751917x14980525963196 ◽

2017 ◽

Keyword(s):

Cascade Reaction ◽

Highly Efficient ◽

Aryl Iodides

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Evaluation of Toxicity in Receiving Streams

Water Science & Technology ◽

10.2166/wst.1992.0736 ◽

1992 ◽

Vol 26 (9-11) ◽

pp. 2357-2360

Author(s):

J. Zagorc-Koncan ◽

M. Dular

Keyword(s):

Dissolved Oxygen ◽

Toxic Substances ◽

Toxicity Evaluation ◽

Copper Cyanide ◽

Polluted River ◽

Design Information ◽

Point Of Entry ◽

Receiving Stream ◽

The Impact

A laboratory river model for the study of self-purification inhibition in a stream containing toxic substances is presented. It enables an engineering - technological prediction of the impact of toxic substances or wastewaters on dissolved oxygen (DO) profile in an organically polluted river downstream from the point of entry of toxic effluent thus providing rapidly and inexpensively significant design information to an environmental scientist or engineer. The method was applied to the toxicity evaluation of wastewaters from electroplating industry. The effects of copper, cyanide (representing two significant constituents of this type of wastewaters) and wastewater from electroplating industry on the biodegradation of organic municipal pollution in receiving stream were evaluated experimentally.

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