Gold versus silver-catalyzed amination of allylic alcohols

Giner, Xavier; Trillo, Paz; Nájera, Carmén

doi:10.1016/j.jorganchem.2010.09.072

Cited by 44 publications

(15 citation statements)

References 19 publications

(11 reference statements)

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“…In 2007, Liu and co‐workers published the first intermolecular allylic amination of tosylamides 31 with alcohols ( 30 ) in the presence of catalytic amounts of AuCl 3 (2 mol %, Scheme a) . Subsequently, a similar strategy was also reported by Nájera and co‐workers …”

Section: Allylic Substitutionscontrasting

confidence: 99%

Gold‐Catalyzed Allylation Reactions

Quintavalla

Bandini

2016

ChemCatChem

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The allylation reaction is a well‐established and indispensable tool for the development of chemical complexity and diversity in organic synthesis. Over several decades, this unique transformation has undergone several developments to establish a more simple, selective, and sustainable variant. Moving from stoichiometric amounts of metal additives to sub‐stoichiometric amounts, and more recently to catalytic loadings is only one of the chemical revolutions faced by the allylation reaction. In this context, homogeneous gold catalysis has played a pivotal role, resulting in unexpected reaction pathways, concerning unactivated unsaturated hydrocarbons, feasible. Among them, [AuI]‐ and [AuIII]‐assisted allylation reactions deserve particular mention owing to their impact in the synthesis of key organic building blocks and value‐added compounds. An unprecedented survey across the development of allylation methodologies based on this coinage metal is documented in the present Minireview.

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Section: Allylic Substitutionscontrasting

confidence: 99%

Gold‐Catalyzed Allylation Reactions

Quintavalla

Bandini

2016

ChemCatChem

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“…Due to the ability of gold complexes to act as σ- and π-acids, gold catalysis gained a prominent role in the activation of allylic alcohols, delivering of water as the side-product. As the topic has been recently extensively reviewed by Aponick and Biannic [7], only the most recent examples of gold-catalyzed manipulation of inactivated allylic alcohols will be discussed here [63–64]. …”

Section: Reviewmentioning

confidence: 99%

New developments in gold-catalyzed manipulation of inactivated alkenes

Chiarucci

Bandini

2013

Beilstein J. Org. Chem.

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SummaryOver the recent years, the nucleophilic manipulation of inactivated carbon–carbon double bonds has gained remarkable credit in the chemical community. As a matter of fact, despite lower reactivity with respect to alkynyl and allenyl counterparts, chemical functionalization of isolated alkenes, via carbon- as well as hetero atom-based nucleophiles, would provide direct access to theoretically unlimited added value of molecular motifs. In this context, homogenous [Au(I)] and [Au(III)] catalysis continues to inspire developments within organic synthesis, providing reliable responses to this interrogative, by combining crucial aspects such as chemical selectivity/efficiency with mild reaction parameters. This review intends to summarize the recent progresses in the field, with particular emphasis on mechanistic details.

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“…Three main catalytic systems have been developed for direct alcohol amination: (i) the borrowing hydrogen method using either Ru or Ir complexes, or non‐noble metal complexes based on Mn or Fe, (ii) Tsuji–Trost type reactions for allylic alcohols using Pd or Ni[6a], complexes, and (iii) Lewis‐acid (LA) catalysts based on a variety of salts and ligands. [2a], [2d] In the latter case, metal triflate [M(OTf) n ] and triflimide [M(NTf 2 ) n ] salts, based on Ca, Al, In, Yb, Bi, Ag, Hg, and HOTf, proved to be efficient. However, the reaction scope is limited to electron‐poor amine derivatives, such as amides, sulfonamides, carbamates and activated alcohols.…”

Section: Introductionmentioning

confidence: 99%

Rational Optimization of Lewis‐Acid Catalysts for Direct Alcohol Amination, Part 2 – Titanium Triflimide as New Active Catalyst

et al. 2020

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The reactivity of a new titanium triflimide salt (see Part 1) was investigated for the direct amination of alcohols. The combination of this new Lewis acid with pyridine‐based ligands allowed a significant increase of activity. The scope of the reaction was increased compared to other Lewis‐acid‐based protocols. Finally, mechanistic insights based on EPR spectroscopy and DFT calculations are provided.

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Gold versus silver-catalyzed amination of allylic alcohols

Cited by 44 publications

References 19 publications

Gold‐Catalyzed Allylation Reactions

Gold‐Catalyzed Allylation Reactions

New developments in gold-catalyzed manipulation of inactivated alkenes

Rational Optimization of Lewis‐Acid Catalysts for Direct Alcohol Amination, Part 2 – Titanium Triflimide as New Active Catalyst

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