Abstract
We report the first regioselective hydrostannation of an aryne.
Excellent yields were achieved under mild room temperature conditions
without the use of additives or catalysts. Preliminary investigations
into the effects of substituents have been conducted, revealing
impressive levels of regiochemical control. The method also offers
a unique route to access 1,2-deuterated arylstannanes demonstrating
the power and potential of this chemistry.
Key words
arynes - hydrostannation - catalyst-free - regioselective - deuterated 1,2-arylstannanes
References and Notes
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General Procedure
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(80%). IR (neat): 2957 (vs), 2926 (vs), 2871 (v), 2853
(v), 1463 (m), 1427 (m), 1376 (m), 1073 (m), 726 (s), 699 (s) cm-¹ . ¹ H
NMR (400 MHz, CDCl3 ): δ = 7.44-7.55
(m, 2 H), 7.32-7.37 (m, 3 H), 1.48-1.68 (m, 6
H), 1.32-1.41 (m, 6 H), 1.00-1.17 (m, 6 H), 0.92
(t, J = 7.3 Hz, 9 H). ¹³ C
NMR (100 MHz, CDCl3 ): δ = 142.0, 136.5,
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The regioselectivity of 10 was confirmed by ¹ H
NMR, COSY, nOe studies and further by carrying out the reaction between 8 and Bu3 SnD, giving n -tributyl(2-deuteride-6-methoxyphenyl)stannane.
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