Triflates cross-coupling

Trifluoropropene, 20 241-242 3-Trifluoroacety 1-17 -camphorate, 6 98 Triflates, cross-coupling of organoboranes with, 73 651 Triflic acid, 22 598 Tri-Flo separator, 76 634 Trifluoroacetylacetone molecular formula, 5 712t Trifluoroacetyl chloride... 

Vinylation can also be done by Pd-catalysed cross-coupling in which one component is used as a halide or triflate and the other as a stannane (Stille reaction) or boronic acid (Suzuki reaction). Entry 9, Table 11.3, is an example of the use of a vinylstannane with a haloindole. lndole-3-boronic acids, which can be prepared by mcrcuration/boration, undergo coupling with vinyl triflates (Entry 10). 

Heck reaction, palladium-catalyzed cross-coupling reactions between organohalides or triflates with olefins (72JOC2320), can take place inter- or intra-molecularly. It is a powerful carbon-carbon bond forming reaction for the preparation of alkenyl- and aryl-substituted alkenes in which only a catalytic amount of a palladium(O) complex is required. 

The key step in a short and efficient synthesis of pleraplysillin-1 (127) is the palladium-catalyzed cross-coupling of vinylstannane 125 with vinyl triflate 126 (see Scheme 33). This synthesis is noteworthy in two respects. First, vinyl triflate 126 is generated regio-specifically from the kinetic enolate arising from a conjugate reduction of enone 124 the conjugate reduction of an enone is, in fact, a... 

TABLE IRON CATALYZED CROSS COUPLING REACTIONS OF GRIGNARD REAGENTS WITH (HETEROJARYL CHLORIDES OR -TRIFLATES... 

Stannyl derivatives of 2ff-pyran-2-one, accessible from bromopyranones by cross coupling with organotin reagents, themselves take part in Pd(0)-catalyscd cross coupling with enol triflates. This methodology offers a new approach to steroidal pyran-2-ones <96JOC6693>. 

Similarly, nickel catalysis permits the extension of cross coupling to vinyl phosphates, which are in some cases more readily obtained and handled than vinyl triflates.273... 

Transition metal-catalyzed transformations are of major importance in synthetic organic chemistry [1], This reflects also the increasing number of domino processes starting with such a reaction. In particular, Pd-catalyzed domino transformations have seen an astounding development over the past years with the Heck reaction [2] - the Pd-catalyzed transformation of aryl halides or triflates as well as of alkenyl halides or triflates with alkenes or alkynes - being used most often. This has been combined with another Heck reaction or a cross-coupling reaction [3] such as Suzuki, Stille, and Sonogashira reactions. Moreover, several examples have been published with a Tsuji-Trost reaction [lb, 4], a carbonylation, a pericyclic or an aldol reaction as the second step. 

The scope of Suzuki-Miyaura reactions is extremely broad, covering practically all types of organic residues. The cross-coupling of arylboronic acids with aryl halides or triflates is the most... 

If the stannane bears substituents at the position geminal to tin, the reaction requires activation by Cu1 (Section 9.6.3.2.1). The cross-coupling of aryl (or heteroaryl) stannanes with aryl (or heteroaryl) halides or triflates is a general route to various biaryls and their analogues, particularly useful in those cases when the Suzuki-Miyaura reaction is less effective for... 

Titanium derivatives were shown to serve as cross-coupling partners for aryl triflates chlorides or bromides, with better tolerance to functional groups than Grignard reagents although specific expensive N,P-chelating ligands are required (Equation (7)) 171... 

Triarylbismuth compounds can be used in cross-coupling reactions with aryl iodides, bromides, or triflates in the presence of Pd(PPh3)4 and CsF or K2C03.174... 

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