2015
DOI: 10.1055/s-0034-1380408
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Catalyst- and Solvent-Free Rapid Addition of Secondary Phosphine Chalcogenides to Aldehydes: Another Click Chemistry

Abstract: An efficient catalyst-and solvent-free method for the synthesis of tertiary α-hydroxyphosphine chalcogenides, via the almost quantitative addition of secondary phosphine chalcogenides to diverse aldehydes under mild conditions (20-52 °C, from 10 min to 5 h), is reported.

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Cited by 30 publications
(14 citation statements)
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“…As could have been expected, a high regioselectivity was detected -the attack of the aldehyde was observed at the methylene group only (Scheme 15). To explore the scope and limitations of this aldol reaction, several activated aldehydes (43) and different substituted 1,3dicarbonyl compounds (44) were subjected (Scheme 16). According to their experiment no aldol reactions were observed on using unactivated aldehydes, like benzaldehyde.…”
Section: Aldol Additions Of 13-dicarbonyl Compoundsmentioning
confidence: 99%
“…As could have been expected, a high regioselectivity was detected -the attack of the aldehyde was observed at the methylene group only (Scheme 15). To explore the scope and limitations of this aldol reaction, several activated aldehydes (43) and different substituted 1,3dicarbonyl compounds (44) were subjected (Scheme 16). According to their experiment no aldol reactions were observed on using unactivated aldehydes, like benzaldehyde.…”
Section: Aldol Additions Of 13-dicarbonyl Compoundsmentioning
confidence: 99%
“…Later, a noncatalyzed version of this reaction was implemented . α‐Hydroxylated tertiary phosphine chalcogenides were synthesized by catalyst‐free addition of R 2 P(E)H (E = S, Se) species to the C=O bond of aldehydes under solvent‐free conditions . In the last year , the noncatalyzed three‐component synthesis of functionalized phosphine sulfides was published from diphenylphosphine, sulfur, and enones in the absence of solvent.…”
Section: Introductionmentioning
confidence: 99%
“…Compound 8 1 H NMR (CDCl3, 400 MHz) δ 10.5 (brs, 1H), 7.84 (dd, J = 3.6, 0.8 Hz, 1H), 7.58 (dd, J = 5.2, 0.8 Hz, 1H), 7.09(dd, J = 5.2, 3.6 Hz, 1H). Synthesis of (Hydroxy(thiophen-2-yl)methyl)diphenylphosphine Oxide (5I)[30] A 50 mL round-bottom flask containing a magnetic stirring bar were added thiophene-2-carbaldehyde (5B: 449 mg, 4.0 mmol, 1.0 equiv) and diphenylphosphine oxide (2A: 809 mg, 4.0 mmol, 1.0 equiv). After stirring the mixture for 4 h at room temperature, the mixture was filtrated.…”
mentioning
confidence: 99%