Multiple methods of synthesizing cannabigerol are presented. Combining olivetol with geraniol derivatives are provided. Cross-coupling methods of combing functionalized resorcinols are provided. Useful intermediates are formed during such cross-coupling steps.

The present invention provides Acyclic diaminocarbene complex of formula (I): ##STR00001##
Wherein, M is palladium; X is monoanionic ligand selected from Cl, Br or I; Where R1 is different from R2; R1 is selected from the group consisting of alkyl or aryl, each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms; R2 is selected from the group consisting of alkyl, or aryl each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms. The said palladium diamino carbine complex of the present invention are particularly useful as catalyst from Hiyama cross-coupling reaction.

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.

The present invention relates to a catalyst composition for synthesis of heteroaromatic biaryls by a light-assisted decarboxylative carbon-carbon cross-coupling reaction, wherein the composition comprises (i) a palladium compound which is selected from a palladium salt or a palladium complex or a mixture thereof, (ii) at least one of the following compounds: a compound of Formula (I)

##STR00001## a compound of Formula (II)

##STR00002## an iridium complex comprising ligands L.sup.1, L.sup.2 and L.sup.3, wherein the ligands L.sup.1, L.sup.2 and L.sup.3 are selected, independently from each other, from a phenylpyridine and a bipyridine.

The invention discloses a tetramethyl-7,7-spirobiindane-based phosphinooxazoline ligand compound and its preparation method and use. The phosphinooxazoline ligand compound is a compound having a structure shown in general formula I or an enantiomer, a raceme or a diastereoisomer thereof. The phosphinooxazoline ligand obtained through a series of reaction steps using cheap and easily available 3,3,3,3-tetramethyl-1,1-spirobiindane-6,6-diol as a starting material. The novel phosphinooxazoline ligand developed in the invention can be used to organic catalytic reactions, especially as a chiral phosphinooxazoline ligand widely used in metal-asymmetric catalytic reactions, having economical practicality and industrial application prospects.

##STR00001##

Lewis acidic metal-organic framework (MOF) materials comprising triflate-coordinated metal nodes are described. The materials can be used as heterogenous catalysts in a wide range of organic group transformations, including Diels-Alder reactions, epoxide-ring opening reactions, Friedel-Crafts acylation reactions and alkene hydroalkoxylation reactions. The MOFs can also be prepared with metallated organic bridging ligands to provide heterogenous catalysts for tandem reactions and/or prepared as composites with support particles for use in columns of continuous flow reactor systems. Methods of preparing and using the MOF materials and their composites are also described.

A long-life catalyst which can be easily and inexpensively manufactured and has high activity and suppressed leakage of metal. A catalyst according to some embodiments includes: a substrate; and a first metal atom as a catalytic center. The substrate contains a non-metallic atom and a second metal atom, and the non-metallic atom is any one selected from the group consisting of a group 15 element, a group 16 element and a group 17 element.

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.

The present invention relates to a Palladium (II)-catalyzed C(sp.sup.3)H alkynylation of amines using picolinamide as directing group. The developed alkynylation strategy is simple, efficient, and tolerant of various ring size including five to eight member cyclic, quaternary amines, and N-heterocyclic motifs.