In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Preparation of Organozinc Reagents via Catalyst Controlled Three-Component Coupling between Alkyne, Iodoarene, and Bis(iodozincio)methane, published in 2017-07-07, which mentions a compound: 175136-62-6, mainly applied to organozinc alkenylzinc reagent preparation protonation boration; alkyne three component coupling iodoarene iodozinciomethane, Application of 175136-62-6.
Three-component coupling between an alkyne, iodoarene, and bis(iodozincio)methane yields allylic Zn with a tetrasubstituted alkene moiety in the presence of a Ni catalyst. The reaction proceeds via aryl nickelation of the alkyne and subsequent cross-coupling with bis(iodozincio)methane. Meanwhile, the same combination in the presence of a Pd and Co catalyst gives tetrasubstituted alkenylzinc. The reaction proceeds via a Pd-catalyzed cross-coupling of iodoarene with bis(iodozincio)methane followed by a Co-catalyzed benzylzincation of alkyne.
Compounds in my other articles are similar to this one(Tris(3,5-bis(trifluoromethyl)phenyl)phosphine)Application of 175136-62-6, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.
Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem