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The Cu-catalyzed oxidative [2+2+1] annulation of 1,n-enynes (n = 6, 7) with α-carbonyl alkyl bromides through C–Br/C–H functionalization has been developed. Using Ag2CO3/tert-butyl hydroperoxide (TBHP) as co-oxidants, α-carbonyl alkyl bromides provide two bonds, the α-C(sp3)–Br bonds and the α-C(sp3)–H bonds, to cyclize with the 1,n-enynes and Cu(MeCN)4PF6, thus forming three new C–C bonds and two rings in a single reaction.

A stable and highly efficient catalyst system consisting of NiCl2(PPh3)2/CuI is used for the Sonogashira reaction of aryl iodides with terminal alkynes which is carried out in a mixture of polyethylene glycol and water with K2CO3 as base to afford a variety of arylacetylenes.

A new copper-catalyzed oxidative difunctionalization of enol ethers with α-amino carbonyl compounds and hydroperoxides is developed. This method is experimentally simple while allowing for regioselective access to 2-amino-3,4-dioxy carbonyl compounds in good yields, and represents the first example of alkene oxyalkylation through C(sp(3))-H functionalization.

The developed reaction system can also be applied to the decarboxylative coupling of cinnamic acid (VII) with cycloalkanes (V) leading to cycloalkylalkenes (VIII).

2,3-Epoxy ketones [(III) and (V)] are synthesized through an oxidative radical pathway with a broad substrate scope and excellent selectivity control.

The crystal and electronic structure of the title compound is investigated by first principle DFT calculations.

The corresponding reaction of an N-acetyl instead of N-methyl substituted 4-aryl-1-alkene derivatives yields only trace amounts of product.

Mono- and difunctionalization of a broad scope of non-activated alkenes is achieved with excellent chemoselectivities by a new oxidative coupling method.

A new palladium-catalyzed oxidative difunctionalization reaction of N-arylalkenes with primary, secondary, and tertiary α-carbonyl alkyl bromides affording indolinones is presented.

A novel, simple route for the synthesis of oxindoles is presented via iron-catalyzed oxidative arylmethylation of activated alkenes with peroxides. This work is realized by the use of a peroxide as the methyl source and 1,4-diazabicyclo[2.2.2]octane as the ligand and represents a new access to oxindoles through an alkene oxidative difunctionalization process.

Di-tert-butyl peroxide is utilized to mediate oxidative 1,2-difunctionalization of activated alkenes (I) and (VI) with an aryl C(sp2)—H and a benzylic C(sp3)—H bond furnishing functionalized oxindols such as (III), (V), and (VIII) in good yields.

Various different functionalized alkynes can be methylated through a C(sp)—C(sp3) bond formation process.

A novel uncatalyzed oxidative cyclization of the N-phenyl acrylamide derivative (I) is developed using tert-butyl hydroperoxide as the oxidant.

An efficient copper-catalyzed intramolecular N-arylation was performed by using substituted 2-(2-bromoaryl)acetamide with a small amount of Cu 2 O and benzene-1,2-diamine as catalytic system under aerobic conditions, which provided good to excellent yields of oxindoles with tolerance of a wide variety of substrates.

Optimized conditions including acetonitrile as the cyanide source and Ag2O/air as the oxidizing agent are developed.

Chiral 2,5-disubstituted bicyclo[2.2.1]heptadiene ligands are prepared and applied to the conjugate addition reaction of arylboronic acids to acyclic α,β-unsaturated compounds.

A new Pd-catalyzed C—H bond activation-annulation-amination tandem method is presented for the synthesis of title compounds (III) and (V).

The first example of the synthesis of indoline-2,3-diones using a transition-metal-catalyzed process is presented.

Nitroarenes can be conveniently reduced to primary amines in good to excellent yields by sodium borohydride in the presence of bismuth chloride or antimony chloride.

Sodium borohydride - bismuth chloride system was applied for the selective reduction of carbon - carbon double bond of α,β - unsaturated esters with high selectivity.

The carbon-carbon double bond that is conjugated to aromatic ring can be conveniently reduced by NaBH4-BiCl3 system in good yields. Aliphatic olefins are inert to this system. This system displays the selective reduction of aromatic olefins in the presence of aliphatic ones.

Aromatic nitro compounds have been found to be selectively reduced to azoxy compounds in good yields by NaBH4 in the presence of bismuth powder.

In the presence of Bu4NBr in DMF solution, the reaction of 3-bromocyclohexene and active metal bismuth from NaBH4 and BiCl3 with aromatic and aliphatic aldehydes provides excellent erythro-selective products.

Metallic antimony catalyzes the reduction of aromatic nitro compounds to the corresponding N-arylhydroxylamines in good yields with NaBH4 under mild conditions. The azoxybenzenes from autoxidation of N-arylhydroxylamines were also obtained in basic conditions.

Derivatives of the lactosyl phosphate diester and the lactosyl thiophosphate diester of 1-(β- d -arabinofuranosyl)cytosine (Ara-C) and 9-(β- d -arabinofuranosyl)adenine (Ara-A) were synthesized by condensation of 3-hydroxypropyl lactoside and a protected Ara-C or Ara-A via H-phosphonate methodology and phosphoramidite methodology, respectively.