Related Experiment Video
Updated: Jul 17, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Efficient and selective nickel-catalyzed addition of H-P(O) and H-S bonds to alkynes
Li-Biao Han1, Chen Zhang, Hideaki Yazawa
1National Institute of Advanced Industrial Science and Technology, Tsukuba, Ibaraki, Japan. libiao-han@aist.go.jp
Abstract:
The cheap nickel catalysts are more reactive than the corresponding noble metal catalysts in the catalytic additions of a variety of P(O)-H bonds and an S-H bond to alkynes, affording regio- and stereoselectively both the Markovnikov and the anti-Markovnikov adducts, respectively, in high yields. A related five-coordinate hydrido nickel complex in the catalysis is successfully isolated, which can react readily with an alkyne to give the addition products.
Related Concept Videos
Catalysis
Leveling Effect and Non-Aqueous Acid-Base Solutions
The Leveling Effect of a Solvent
A generic acid (HA) reacts with the generic base (B-) to yield the corresponding conjugate base (A-) and conjugate acid (HB):
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Catalysis
Heterogeneous Catalysis

