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A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.

The trifluoromethylation of benzoic acids with TMSCF3 was achieved through nucleophilic substitution with the use of anhydrides as an in situ activating reagent. Under the reaction conditions, a wide range of carboxylic acids including the bioactive ones worked well, thus providing a facile and efficient method for preparing aryl trifluoromethyl ketones from the readily available starting materials.

A palladium-catalyzed decarbonylative alkenylation of aromatic carboxylic acids was developed. Under the reaction conditions, various benzoic acids including those bearing functional groups coupled to terminal alkenes, producing the corresponding internal alkenes in good to high yields. Cinnamic acids and bioactive benzoic acids such as 3-methylflavone-8-carboxylic acid, probenecid, adapalin, and febuxostat were also applicable to this reaction, demonstrating the potential synthetic value of this new reaction in organic synthesis.

A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.

A direct phosphorylation of the sp3C-CN bond catalyzed by a nickel catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.

A direct phosphorylation of the sp

A palladium-catalyzed decarbonylative alkynylation of amides via C–N bond activation is developed. Compared with the reported Ni/Cu catalyzed reaction, which only proceeded well with silylacetylenes, this transformation was also applicable to both aromatic and aliphatic terminal alkynes, including those bearing functional groups, and thus provided a general and straightforward access to diverse internal alkynes.

The Ni-catalyzed direct C-H/C-O cross couplings of benzylic alcohol derivatives with fluorobenzenes and heteroarenes are disclosed. This transformation provides a straightforward and efficient method for the synthesis of these valuable heteroatom-containing compounds.

An efficient one-pot synthesis of α-acyloxyphosphoryl compounds from aldehydes and hydrogen phosphoryl compounds has been developed using a facile base-mediated redox strategy. This redox transformation is applicable to synthesize a wide range of valuable α-acyloxyphosphoryl compounds with high atom- and step-economic efficiency.

An efficient synthesis of 2-hetarylquinazolin-4(3H)-ones via copper-catalyzed direct aerobic oxidative amination of sp(3)C-H bonds has been developed. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 2-hetaryl-substituted quinazolinones from easily available 2-aminobenzamides and (2-azaaryl)methanes.