Silver‐Catalyzed Hydroamination: Synthesis of <i>N</i>‐Bridgehead Pyrroles, Incorporating a Protection‐Deprotection Strategy for Preparation of Cyclic Secondary Vinylogous Carbamates

Robinson, Ross S.; Dovey, Martin C.; Gravestock, David

doi:10.1002/ejoc.200400598

Cited by 55 publications

(16 citation statements)

References 23 publications

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“…Dovey and coworkers utilized silver mediated hydroamination triggered cyclization strategy for the preparation of N-fused pyrroles 50 from vinylogous carbamate 49 and propargyl bromide (Scheme 13) [50]. The reaction was believed to proceed via intermolecular hydroamination of the triple bond of propargyl bromide (cf.…”

Section: Reactions Triggered By Intermolecular Hydroaminationmentioning

confidence: 98%

Alkyne hydroamination triggered cyclizations: A powerful tool for the construction of biologically important structural motifs

Patil

Singh

2011

Journal of Organometallic Chemistry

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Section: Reactions Triggered By Intermolecular Hydroaminationmentioning

confidence: 98%

Alkyne hydroamination triggered cyclizations: A powerful tool for the construction of biologically important structural motifs

Patil

Singh

2011

Journal of Organometallic Chemistry

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“…Silver catalyzed intermolecular hydroaminations of alkynes using cyclic secondary vinylogous carbamates to give enamines [811]. Silver catalyzed a sequential hydroamination-cyclization of aryl alkynes with aryl amines (Eq.…”

Section: Formation Of Carbon-nitrogen Bonds From Alkenes Alkynes Anmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…[7] This finding is especially noteworthy as silverbased catalysts have not been used extensively for the hydroamination of alkynes and alkenes. [8] The hydroamination product, 3, was obtained in 86 % yield after 30 min at room temperature by using only 1 mol % of AgNTf 2 ( Table 1, entry 4). The catalyst loading could be further decreased to 0.3 mol % without significant loss of efficiency (Table 1, entry 5).…”

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confidence: 99%

Silver‐Catalyzed Hydroamination of Siloxy Alkynes

Sun

Kozmin

2006

Angew Chem Int Ed

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Transition-metal-catalyzed hydroamination of alkynes has emerged as a valuable method for C À N bond formation. [1] While significant progress in this area has been made, [2] several important limitations remain to be addressed. The majority of the previously developed catalytic processes employ highly nucleophilic primary amines that afford the corresponding imines as a result of tautomerization of the initially produced enamides. [3][4][5] We describe herein the first example of hydroamination of electron-rich alkynes by using a silver-based catalyst that enables syn-selective addition of secondary amides and carbamates to furnish the corresponding silyl ketene aminals with high efficiency and excellent diastereoselectivity. Our mechanistic studies demonstrate that the reaction proceeds by a fast and reversible silveralkyne complexation, followed by a rate-determining CÀN bond-forming step, which provides an important mechanistic platform for further development of d 10 catalysts for alkyne and alkene hydroamination.During our continuing investigation of the development of new catalytic CÀC and CÀX bond-forming reactions with electron-rich alkynes, [6] we discovered that treatment of siloxy alkyne 1 (TIPS = iPr 3 Si) with carbamate 2 in the presence of either a silver-or a gold-based catalyst resulted in the formation of silyl ketene aminal 3 (Table 1). Initial investigations revealed that the use of AgNTf 2 (Tf = CF 3 SO 2

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Silver‐Catalyzed Hydroamination: Synthesis of N‐Bridgehead Pyrroles, Incorporating a Protection‐Deprotection Strategy for Preparation of Cyclic Secondary Vinylogous Carbamates

Abstract: N-Bridgehead pyrroles are efficiently prepared from cyclic secondary vinylogous carbamates using a two-step sequence. This sequence involves C-propargylation followed by a silver-catalyzed intramolecular hydroamination. Hydroamination is brought about using microwave irradiation

Cited by 55 publications

References 23 publications

Alkyne hydroamination triggered cyclizations: A powerful tool for the construction of biologically important structural motifs

Alkyne hydroamination triggered cyclizations: A powerful tool for the construction of biologically important structural motifs

Transition metals in organic synthesis: Highlights for the year 2005

Silver‐Catalyzed Hydroamination of Siloxy Alkynes

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