Phenylsilane as an active amidation reagent for the preparation of carboxamides and peptides

Ruan, Zheming; Lawrence, R. Michael; Cooper, Christopher B.

doi:10.1016/j.tetlet.2006.08.024

Cited by 49 publications

(25 citation statements)

References 7 publications

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“…Interestingly, employing either 0.5 or 1.5 equiv of PhSiH 3 led to a reduction in the yield of 3 a (Table 1, entries 6 and 7). The observation that 4 equiv of PhSiH 3 prevented amide formation indicates that minimizing competitive aza‐ylide reduction is critical (Table 1, entry 9) 10…”

Section: Methodsmentioning

confidence: 99%

Phosphine‐Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides

2012

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Section: Methodsmentioning

confidence: 99%

Phosphine‐Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides

2012

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“…Alternatively, the carboxamide could be formed by reaction of an activated carboxylic acid and an adjacent amine. It has been reported carboxylic acid could be activated by reaction with phenylsilane [32] or tetrakis(pyridine-2-yloxy)silane [33] to form silyl esters which coupled with amines to form amides. In the case of Paired(COOH)(NH), the carboxylic acid could have been activated by reaction with silazane to form the silyl ester, which reacted with a nearby amine to form an amide.…”

Section: Paired (Cooh)(nh)mentioning

confidence: 99%

Synthesis and characterization of bifunctional surfaces with tunable functional group pairs

Galloway

Kung

2016

Surface Science

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Grafting of pairs of functional groups onto a silica surface was demonstrated by tethering both terminals of an organochlorosilane precursor molecule, Cl 2 (CH 3)Si(CH 2) 4 (CO)(OSi(i-Pr) 2)(CH 2) 2 Si(CH 3)Cl 2 , that possess a cleavable silyl ester bond, onto a silica surface. Hydrolytic cleavage of the silyl ester bond of the grafted molecule resulted in the generation of organized pairs of carboxylic acid and organosilanol groups. This organosilanol moiety was easily transformed into other functional groups through condensation reactions to form, together with the neighboring acid group, pairs such as carboxylic acid/secondary amine, carboxylic acid/pyridine, and carboxylic acid/phosphine. In the case of carboxylic acid/amine pairing, there was evidence of the formation of amide. A sample grafted with amine-carboxylic acid pairs was three times more active (per free amine) than a sample without such pairs for the nitroaldol condensation of 4-nitrobenzaldehyde and nitromethane.

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“…7 It can also act as an in situ carboxylic acid activating agent to prepare carboxamides and peptides from carboxylic acids and amines. 8 Phenylsilane is commercially available now. It can be readily prepared by reduction of phenyltrichlorosilane with lithium aluminum hydride in ether.…”

Section: Introductionmentioning

confidence: 99%

Phenylsilane

Li¹

2011

Synlett

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Phenylsilane as an active amidation reagent for the preparation of carboxamides and peptides

Cited by 49 publications

References 7 publications

Phosphine‐Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides

Phosphine‐Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides

Synthesis and characterization of bifunctional surfaces with tunable functional group pairs

Phenylsilane

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