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 application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect.

##STR00001##

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 method for C—H bond activation and/or C—N coupling reaction comprises using a metal catalyst to catalyze the C—H bond activation and/or C—N coupling reaction; wherein the metal catalyst represented by the following formula a metal catalyst for C—H bond activation and/or C—N coupling reaction, and a method using the same and application thereof. Specifically, a metal catalyst represented by the following formula:

##STR00001## wherein Q is a 5 or 6 membered aromatic ring; W, X, and Y are the same or different, and are independently N, S, P, or O; M is Ni, Pd, Fe, Co, Cr, Mn, Cu, Pt, Ir, or Ru; Z is halide (F, Cl, Br, or I), acetate, water, or hydroxyl; R.sub.1 and R.sub.2 are the same or different, and are independently alkyl, aryl, alkylaryl or cycloalkyl.

This disclosure relates to synthetic coupling methods using catalytic molecules. In certain embodiments, the catalytic molecules comprise heterocyclic thiolamide, S-acylthiosalicylamide, disulfide, selenium containing heterocycle, diselenide compound, ditelluride compound or tellurium containing heterocycle. Catalytic molecules disclosed herein are useful as catalysts in the transformation of hydroxy group containing compounds to amides, esters, ketones, and other carbon to heteroatom or carbon to carbon transformations

The invention relates to ylide-functionalized phosphane ligands, the production of same and use in transition metal compounds, as well as the use of same as catalysts in organic reactions.

The invention relates to ylide-functionalized phosphane ligands, the production of same and use in transition metal compounds, as well as the use of same as catalysts in organic 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 method for producing a compound represented by formula (4)

##STR00001##

[R.sup.1-R.sup.5 represent hydrogen atoms, formula (2), or formula (5), and at least one of R.sup.1-R.sup.5 is a group represented by formula (5) (Ar.sup.1Ar.sup.3 are the same as below)],

##STR00002##

the method comprising carrying out deprotection after reacting an amine compound represented by formula (1)

##STR00003##

[R.sup.1-R.sup.5 each independently represent a hydrogen atom or a group represented by formula (2)

##STR00004##

(Ar.sup.1 and Ar.sup.2 represent aryl groups and Ar.sup.3 represents an arylene group, and any two of Ar.sup.1-Ar.sup.3 may bond to form a ring), and at least one of R.sup.1-R.sup.5 is a hydrogen atom] with a compound represented by formula (3)

##STR00005##

(X represents a halogen atom, etc., and R.sup.6-R.sup.8 represent an alkyl group, etc.) in the presence of a catalyst and a base, is a method for producing an aniline derivative suited to efficient industrial production that does not require a large excess of base and oxygen in the process of deprotection.

In one aspect, the disclosure relates to a mode of asymmetric induction in radical processes based on sequential combination of enantiodifferentiative H-atom abstraction and stereoretentive radical substitution. Also disclosed is an asymmetric system for stereoselective synthesis of strained 5-membered cyclic sulfamides via radical 1,5-CH amination of sulfamoyl azides. The disclosed metalloradical system can control the degree and sense of asymmetric induction in the catalytic radical CH amination in a systematic manner. The disclosed system is applicable to a broad scope of substrates with different types of C(sp.sup.3)-H bonds and exhibits reactivity and selectivity, providing access to both enantiomers of useful 5-membered cyclic sulfamides in a highly enantioenriched form. Also disclosed are catalysts useful in these processes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.