In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

Gold (I) complexes that can absorb light in the near-UV and/or visible regions and methods of making and using thereof are described. These gold (I) complexes have photochemical reactivities, such as strong absorption of near-UV and/or visible light, quenching rate constants ≥3.5×10.sup.5 s.sup.−1, etc., that allow them to catalyze photoredox reactions, such as homocoupling of organic halides (e.g. alkyl halides and aryl halides), alkylation of 2-phenyl-1,2,3,4-tetrahydroisoquinoline, cyclization of indoles, reductive dehalogenation of aryl halides, and/or C—H bonds cleavage, under near-UV and/or visible light. The product of a photo-induced organic reaction catalyzed by the gold (I) complexes described herein can have a yield that is higher than the yield of the same product formed from the same reaction under the same reaction conditions, using the same loading or a higher loading of [Au.sub.2(μ-dppm).sub.2](Cl).sub.2, [Ru(bpy).sub.3](Cl).sub.2, and/or [fac-Ir(ppy).sub.3] compared to the loading of the one or more gold (I) complex(es).

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

A process can be used to produce N-vinyl compounds by homogeneous catalysis. In the process, acetylene is reacted with a cyclic compound having at least one nitrogen as a ring member, hearing a substitutable hydrogen residue (cyclic compound C), in a liquid phase in the presence of a ruthenium complex containing at least one phosphine as a ligand (RuCat).

Disclosed is a method for producing a mono-cross-coupled aromatic compound (3-1) having one less leaving group than an aromatic compound (1) having at least two leaving groups, the method comprising: preparing the aromatic compound (1) having at least two leaving groups; preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic boronic acid (2-1), an aromatic amino compound (2-2), a diboronic acid ester (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; and performing a cross-coupling reaction of the aromatic compound (1) having at least two leaving groups with the compound (2) in the presence of a palladium catalyst and a base, in the absence of a solvent.

The present invention provides a palladium(II) complex of formula (1). ##STR00001## R.sub.12, m, and X are described in the specification. The invention also provides a process for the preparation of the complex, and its use in carbon-carbon and carbon-heteroatom coupling reactions.

The present invention provides a palladium(II) complex of formula (1). ##STR00001## R.sub.12, m, and X are described in the specification. The invention also provides a process for the preparation of the complex, and its use in carbon-carbon and carbon-heteroatom coupling reactions.

The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and/or stereoselectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and Z-selectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and E-selectivity. In some embodiments, provided technologies are particularly useful for preparing alkenyl fluorides. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-a. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-b.