Copper-promoted CN bond cross-coupling with phenylstannane

Lam, Patrick Y.S.; Vincent, Guillaume; Bonne, Damien; Clark, C. G.

doi:10.1016/s0040-4039(02)00356-8

Cited by 87 publications

(32 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[95] However, the yields are modest and in some cases the reaction completely fails. In most cases, even after prolonged heating, homocoupling was a major side reaction.…”

Section: Aryl Stannanes As the Aryl Donor: C(aryl)-heteroatom Bond Fomentioning

confidence: 99%

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

Ley,

Thomas

2003

Angew Chem Int Ed

2,492

816

View full text Add to dashboard Cite

The copper-mediated C(aryl)[bond]N, C(aryl)[bond]O, and C(aryl)[bond]S bond formation is an important transformation and has been developed to include a wide range of substrates. This Review highlights the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids, aryl halides, iodonium salts, siloxanes, stannanes, plumbanes, bismuthates, and trifluoroborate salts as aryl donors. In particular, the recent introduction of boronic acids as reaction partners in both O- and N-arylation has been a significant discovery and will occupy centre-stage in this review. Clear improvements can be obtained by the correct choice of copper source, base, ligands, and other additives. Mechanistic investigations should provide insight into the catalytically active species, which would aid in the development of milder, more-efficient methods.

show abstract

“…[95] However, the yields are modest and in some cases the reaction completely fails. In most cases, even after prolonged heating, homocoupling was a major side reaction.…”

Section: Aryl Stannanes As the Aryl Donor: C(aryl)-heteroatom Bond Fomentioning

confidence: 99%

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

Ley,

Thomas

2003

Angew Chem Int Ed

2,492

816

View full text Add to dashboard Cite

show abstract

“…These reactions have the advantage of taking place under mild conditions (often at room temperature under neutral conditions) 9,62,63 and have been utilized in some elegant natural product syntheses. 64–66 A number of aryl donors have been employed in these reactions including aryl stannanes, 67 aryl bismuth reagents, 68 aryl siloxanes 69 and diaryl iodonium salts. 70 These reactions can offer unrivalled functional group tolerance, however, the expense and difficulty of access to the arylating agents can represent a serious limitation.…”

Section: Introductionmentioning

confidence: 99%

Diamine ligands in copper-catalyzed reactions

2010

View full text Add to dashboard Cite

The utility of copper-mediated cross-coupling reactions has been significantly increased by the development of mild reaction conditions and the ability to employ catalytic amounts of copper. The use of diamine-based ligands has been important in these advances and in this review we discuss these systems, including the choice of reaction conditions and applications in the synthesis of pharmaceuticals, natural products and designed materials.

show abstract

“…Alternatively, 32 is more likely to undergo air oxidation to yield the corresponding higher oxidation-state copper(III) complex 34, which can now more efficiently reductively eliminate to afford product 33. When the organometalloid is phenyltrimethoxysiloxane [55] instead of phenylboronic acid, we have titrated for copper(0) and found only trace amount. Presumably, most of the copper at the end of the reaction is in the form of copper(I).…”

Section: Mechanismmentioning

confidence: 99%

“…Other organometalloids that can also participate in this copper-promoted cross-coupling reaction are aryltrialkylsiloxanes [51b, 54], aryltrimethylstannanes [55], triarylbismuths [5,56], arylleads [57], diaryliodonium salts [58a], diethylzinc [58b] and dialkylaluminum chlorides [58c].…”

Section: Other Organometalloidsmentioning

confidence: 99%