Bismuth(III) chloride-aluminum-promoted alkylations of immonium cations to amines in aqueous media: unstabilized carbanion equivalents for use in the presence of water

Katritzky, Alan R.; Shobana, N.; Harris, Philip A.

doi:10.1021/om00039a049

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Cited by 41 publications

(11 citation statements)

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“…There is no need for protection/deprotection of groups that minimizes reaction steps. There are many metals such as indium, 11 bismuth, 12 and zinc 13 which are used for allylation reaction and tin is the best for industrial applications because of its low cost, ready availability and relatively low toxicity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of active tin: an efficient reagent for allylation reaction of carbonyl compounds

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Synthesis of active tin: an efficient reagent for allylation reaction of carbonyl compounds

et al. 2015

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“…2 The most commonly used metals are zinc, tin, indium and bismuth or BiCl 3 ^Al, BiCl 3 ^Zn and BiCl 3 ^Fe systems. 3 However, the type of aqueous organometallic reactions seems to have been somewhat limited. It has been used mainly in Barbier-type reactions.…”

mentioning

confidence: 99%

A Novel Synthesis of Allyl Sulfides and Allyl Selenides via Sm–BiCl3 System in Aqueous Media

Zhan¹,

Lu²,

Zhang³

1999

J. Chem. Res.

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“…For example, tin [18], bismuth(III)-aluminum system [19], indium [20] or zinc [21] have all been used for the allylation of iminium cations to give homoallyl amines in water [22].…”

Section: Introductionmentioning

confidence: 99%

Unorthodox chemistry for an unorthodox challenge: Exploration of new chemical reactivities for a sustainable future

2011

Sci. China Chem.

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The sustainable development of our future represents an unorthodox challenge in sciences and technologies. The exploration of unconventional chemical reactivities that could potentially result in more sustainable chemical productions with efficient utilization of resource and inherent prevention of waste will provide the foundation for the synthetic chemistry of our future. As part of this endeavor, we have explored metal-mediated reactions in water to minimize protection-deprotection and the use of organic solvents, catalytic nucleophilic additions via C-H reactions to avoid generation and use of stoichiometric organic halides and metal in water, and Cross-Dehydrogenative-Coupling (CDC) reactions to minimize overall transformation steps. green chemistry, organometallic reactions in water, aldehyde-alkyne-amine coupling, cross-dehydrogenative-coupling

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Bismuth(III) chloride-aluminum-promoted alkylations of immonium cations to amines in aqueous media: unstabilized carbanion equivalents for use in the presence of water

Cited by 41 publications

References 0 publications

Synthesis of active tin: an efficient reagent for allylation reaction of carbonyl compounds

Synthesis of active tin: an efficient reagent for allylation reaction of carbonyl compounds

A Novel Synthesis of Allyl Sulfides and Allyl Selenides via Sm–BiCl3 System in Aqueous Media

Unorthodox chemistry for an unorthodox challenge: Exploration of new chemical reactivities for a sustainable future

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