Barbier-type allylation of iminium ions generated in situ in aqueous medium

Estevam, Idália Helena Santos; Bieber, Lothar W.

doi:10.1016/s0040-4039(02)02667-9

Cited by 52 publications

(10 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Iminium ions, generated in aqueous solution from secondary amines and formaldehyde, undergo a Bar- bier-type allylation mediated by tin, aluminum, and zinc (eq 150). The reaction is catalyzed by copper and produces tertiary homoallylamines in up to 85% yield . The imines, generated in situ from 2-pyridinecarboxaldehyde/2-quinolinecarboxaldehyde and arylamines, undergo indium-mediated Barbier allylation in aqueous media to provide homoallylic amines …”

Section: 12 Addition Of Allyl Groupsmentioning

confidence: 99%

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

2005

Chem. Rev.

2,187

641

View full text Add to dashboard Cite

Section: 12 Addition Of Allyl Groupsmentioning

confidence: 99%

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

2005

Chem. Rev.

2,187

641

View full text Add to dashboard Cite

“…A reasonable amount of allylic bromide is found to be 2.0 equiv. (Table 1, entries [6][7][8]. It is worth noticing that 5a is always formed in a yield of around 20% in every experiment when the ratio of aniline and benzaldehyde is fixed at 1/1 ( Table 1, entries 3-8).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of homoallylic amines and acylhydrazides by tin powder‐promoted multicomponent one‐pot allylation reactions

Huang

Wang

et al. 2016

Applied Organom Chemis

View full text Add to dashboard Cite

An efficient process for the synthesis of homoallylic amines and N′-homoallylic hydrazides is developed from the one-pot reaction of carbonyl compounds, amines or N-acylhydrazines, allyllic bromide and tin powder using water as solvent. N-Acylhydrazines are found to be more reactive than amines in these processes. They can react not only with aldehydes but also with ketones to give the corresponding N′-homoallylic hydrazides.

show abstract

“…Moreover, Lewis acids or Brønsted acids are often needed in the allylation of imines with allyltributyltin to activate the substrates, [52][53][54][55][56][57][58][59][60][61] generally because of the lower reactivity of imine compared with the corresponding aldehyde. [65] Herein, we report a one-pot four-component procedure for preparation of homoallylic amines, involving in situ generation [66][67][68] of imines and allyltin without any additive. As we know, tin powder is much less toxic than the organostannes.…”

Section: Introductionmentioning

confidence: 99%

“…To our knowledge, there are few reports on four-component allylation in the presence of tin powder. [65] Herein, we report a one-pot four-component procedure for preparation of homoallylic amines, involving in situ generation [66][67][68] of imines and allyltin without any additive.…”

Section: Introductionmentioning

confidence: 99%