Butyltellurium Tribromide: A Suitable Electrophilic Source to Cyclization Reactions

Abstract

We present here our results of the electrophilic cyclization reaction of (Z)-chalcogenoenynes using butyltellurium tribromide as an electrophilic source. The cyclization reaction proceeded cleanly under mild reaction conditions and 3-(butyltellanyl)chalcogenophenes were formed in moderate to excellent yields. Subsequent, using these heterocycles as substrate to palladium-catalyzed cross-coupling reactions a new carbon-carbon bond was formed in good yields.

Key words

tellurium - electrophilic cyclization - chalcogenophenes

References and Notes

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8

General Procedure for the BuTeBr ₃ Cyclizations
To a solution of 0.50 mmol of the appropriate (Z)-selenoenyne in MeCN (5 mL) was added BuTeBr₃ (0.233 g, 0.55 mmol). The reaction mixture was allowed to stir at r.t. for the time showed in Table [3] . After this time, EtOH (5 mL) and NaBH₄ (0.037 g, 1 mmol) were added under vigorous stirring (gas evolution was observed during this addition). The reaction mixture was stirred at r.t. for one additional hour, diluted with EtOAc (20 mL) and washed with H₂O (10 mL) and brine (3 × 10 mL). The organic layer was dried over anhyd Mg₂SO₄ and concentrated under vacuum to yield the crude product, which was purified by flash chromatography on silica gel using hexane as the eluent.
Analysis of the ¹H NMR and ¹³C NMR spectra showed that all the obtained products presented data in full agreement with their assigned structures.
Selected Spectral and Analytical Data for 2b
Yield 0.212g (91%). ¹H NMR (200 MHz, CDCl₃): δ = 7.51-7.49 (m, 5 H), 7.44-7.28 (m, 6 H), 2.79 (t, J = 7.6 Hz, 2 H), 1.67 (quin, J = 7.6 Hz, 2 H), 1.29 (sext, J = 7.6 Hz, 2 H), 0.84 (t, J = 7.6 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 150.92, 150.21, 137.67, 135.75, 135.14, 129.31, 128.93, 128.25, 127.97, 127.76, 126.20, 104.55, 36.64, 24.88, 13.32, 8.88. MS: m/z (rel. intensity) = 468 (37), 411 (11), 284 (72), 202 (100), 77 (6), 57 (5). HRMS: m/z calcd for C₂₀H₂₀SeTe: 469.9792; found: 469.9798.