Suyan Sun

Copper(I)-Catalyzed Sulfonylation of 8-Aminoquinoline Amides with Sulfonyl Chlorides in Air.

A simple and mild protocol for copper(I)-mediated sulfonylation of 8-aminoquinoline amides with sulfonyl chlorides was developed, affording desired products in moderate to good yields. This reaction proceeds in air and features excellent substrate tolerance, especially for aliphatic sulfonyl chlorides.

Silver(I)-promoted C5–H phosphonation of 8-aminoquinoline amides with H-phosphonates

A simple and efficient protocol for silver(I)-promoted phosphonation of 8-aminoquinoline amides with dialkyl H-phosphonates has been developed, affording the desired products in moderate yields. This method features C5–H regioselectivity of 8-aminoquinoline amides, a broad substrate scope and general functional group compatibility.

Palladium-Catalyzed Regioselective C8–H Amination of 1-Naphthylamine Derivatives with Aliphatic Amines

A simple and facile protocol for palladium-catalyzed picolinamide-directed C8-H amination of 1-naphthylamine derivatives with simple secondary aliphatic amines was developed, thereby providing a new route to 1,8-naphthalenediamine derivatives. It is noteworthy that the picolinamide moiety as a bidentate directing group may play a key role in this regioselective transformation.

Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

A simple and efficient protocol for the transition metal-catalyzed site-selective C–H phosphonation of 8-aminoquinolines with diarylphosphine oxide or H-phosphonate diesters was developed via a photoredox process. This reaction features high regioselectivity at the C4 or C5 position under mild and simple conditions (with a catalytic amount of silver salt at room temperature). Note that the C4 position of 8-aminoquinoline is an unusual reactive site.

Ru/Cu Photoredox or Cu/Ag Catalyzed C4–H Sulfonylation of 1-Naphthylamides at Room Temperature

A mild and efficient protocol for C4-H sulfonylation of 1-naphthylamine derivatives with sodium sulfinates has been described. This C4 sulfonylation proceeded smoothly at room temperature under Ru/Cu photoredox catalysis or Cu/Ag cocatalysis and could tolerate various functional groups. In addition, control experiments suggested that this C4-H sulfonylation reaction might proceed via a single-electron-transfer process.

One-pot synthesis of unsymmetrical diarylacetylenes via Sonogashira/deacetonation/Sonogashira cross-coupling of two different aryl chlorides with 2-methyl-3-butyn-2-ol

With the assistance of PdCl2/X-Phos as the catalyst system, a green and efficient protocol for one-pot Sonogashira/Deacetonation/Sonogashira coupling reaction of two different aryl chlorides with 2-methyl-3-butyn-2-ol was developed, affording various unsymmetrical diarylacetylenes in mostly moderate to excellent yields. Note that the cheap and economically available aryl chlorides and 2-methyl-3-butyn-2-ol as the starting materials could be added to the catalyst system directly and simultaneously. Moreover, this tandem reaction could tolerate substrates bearing one or even two ortho-sterically hindered groups and was also applicable to the synthesis of symmetrical diarylacetylenes. In addition, the competitive reaction was performed and a possible mechanism was also proposed.

Palladium-catalyzed direct C–H arylation of ferrocenecarboxamides with aryl halides

A simple and facile protocol for the palladium-catalyzed ortho-arylation of ferrocenecarboxamides with aryl halides was developed with the assistance of the bidentate directing group. The substrate scope could be extended to aryl iodides, bromides and even chlorides, as well as heterocyclic halides, affording diarylated products in moderate to good yields.

Silver(I)-Catalyzed C4–H Amination of 1-Naphthylamine Derivatives with Azodicarboxylates

A simple and efficient protocol for silver(I)-catalyzed picolinamide directed C4-H amination of 1-naphthylamine derivatives with readily available azodicarboxylates has been developed, demonstrating a new approach to 1,4-naphthalenediamine derivatives in high yields. Note that this reaction system could proceed under external-oxidant- and additive-free conditions (only requires 5 mol % of AgOAc as the catalyst in acetone).

Pd-catalyzed aminocarbonylation of alkynes with amines using Co2(CO)8 as a carbonyl source

A simple and mild protocol for the synthesis of 2-ynamides by palladium-catalyzed aminocarbonylation of alkynes was developed. The reaction proceeded at room temperature in air, utilizing Co2(CO)8 as a carbonyl source. This aminocarbonylation reaction features mild reaction conditions and good tolerance of substrates especially including aryl amines and primary amines.