A general and efficient method for the copper-catalyzed cross-coupling of amides and thiophenols with 6-halogenoimidazo[1,2-a]pyridines

Enguehard‐Gueiffier, Cécile; Thery, Isabelle; Gueiffier, Alain; Buchwald, Stephen L.

doi:10.1016/j.tet.2006.04.007

Cited by 50 publications

(10 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Many other efficient systems, although they can be considered as making significant contributions to the field, are outside the scope of this Minireview. [34][35][36][37][38] 2.1.1. Coupling Reactions of Aryl Halides with N Heterocycles 2.1.1.1.…”

Section: Ullmann Coupling Under Homogeneous Conditions 21 Càn Bond mentioning

confidence: 99%

Catalytic CC, CN, and CO Ullmann‐Type Coupling Reactions

2009

View full text Add to dashboard Cite

Copper-catalyzed Ullmann condensations are key reactions for the formation of carbon-heteroatom and carbon-carbon bonds in organic synthesis. These reactions can lead to structural moieties that are prevalent in building blocks of active molecules in the life sciences and in many material precursors. An increasing number of publications have appeared concerning Ullmann-type intermolecular reactions for the coupling of aryl and vinyl halides with N, O, and C nucleophiles, and this Minireview highlights recent and major developments in this topic since 2004.

show abstract

Section: Ullmann Coupling Under Homogeneous Conditions 21 Càn Bond mentioning

confidence: 99%

Catalytic CC, CN, and CO Ullmann‐Type Coupling Reactions

2009

View full text Add to dashboard Cite

show abstract

“…Over the last decade, copper has emerged as a viable catalyst for the arylation of thiols. [ 27 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 , 99 , 100 , 101 , 102 , 103 ] Palomo and co-workers demonstrated the ability of CuBr with phosphazene base to catalyze reaction between aryl iodides and thiols to afford biaryl sulfides Equation (12) [ 67 ]. Activated aryl bromides were also effective as coupling partners.…”

Section: Copper-catalyzed Arylation Of Thiolsmentioning

confidence: 99%

Transition Metal Catalyzed Synthesis of Aryl Sulfides

2011

View full text Add to dashboard Cite

The presence of aryl sulfides in biologically active compounds has resulted in the development of new methods to form carbon-sulfur bonds. The synthesis of aryl sulfides via metal catalysis has significantly increased in recent years. Historically, thiolates and sulfides have been thought to plague catalyst activity in the presence of transition metals. Indeed, strong coordination of thiolates and thioethers to transition metals can often hinder catalytic activity; however, various catalysts are able to withstand catalyst deactivation and form aryl carbon-sulfur bonds in high-yielding transformations. This review discusses the metal-catalyzed arylation of thiols and the use of disulfides as metal-thiolate precursors for the formation of C-S bonds.

show abstract

“…The iodinated compound 8a was also reactive toward copper-catalyzed cross-coupling with benzamide or thiophenol, giving 15 and 16 in 57% and 98% yields, respectively, under the previously described conditions ( Table 3, entries 4 and 5, respectively). 8 Finally, a nitrile group was successfully introduced in the 4-position of compounds 8a and 8b by treatment with copper(I) cyanide (1.3 equiv) in N,N-dimethylformamide with microwave irradiation at 200 °C for 15 minutes, giving 90% and 94% yields, respectively, of the cyano derivatives 17 and 18 (Table 3, entries 6 and 7).…”

Section: Paper Syn Thesismentioning

confidence: 99%

Domino 6-endo-dig Cyclization/Halogenation Reactions: Three-Component Synthesis of 1,3-Disubstituted 4-Haloimidazo[1,2-a:4,5-c′]dipyridines

et al. 2015

Self Cite

View full text Add to dashboard Cite

A regiocontrolled 6-endo-dig cyclization of 3-ethynylimidazo[1,2-a]pyridine-2-carbonitriles promoted by Grignard reagent in the presence of iodine has been developed. We optimized the reaction conditions to allow the straightforward synthesis of 1,3-disubstituted 4-iodoimidazo[1,2-a:4,5-c′]dipyridines. Finally, the reactivity of the 4-iodo position toward various metal-catalyzed coupling reactions (Suzuki-Miyaura, Sonogashira, etc.) or cyanation was successfully evaluated.

show abstract

A general and efficient method for the copper-catalyzed cross-coupling of amides and thiophenols with 6-halogenoimidazo[1,2-a]pyridines

Cited by 50 publications

References 23 publications

Catalytic CC, CN, and CO Ullmann‐Type Coupling Reactions

Catalytic CC, CN, and CO Ullmann‐Type Coupling Reactions

Transition Metal Catalyzed Synthesis of Aryl Sulfides

Domino 6-endo-dig Cyclization/Halogenation Reactions: Three-Component Synthesis of 1,3-Disubstituted 4-Haloimidazo[1,2-a:4,5-c′]dipyridines

Contact Info

Product

Resources

About