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The partial reduction of electron-deficient pyrroles: procedures describing both Birch (Li/NH3) and ammonia-free (Li/DBB) conditions

Timothy J Donohoe & Rhian E Thomas

Nature Protocols 2, 1888 - 1895 (2007) Published online: 2 August 2007

doi:10.1038/nprot.2007.245

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Figure 1 - Unfortunately we are unable to provide accessible alternative text for this. If you require assistance to access this image, or to obtain a text description, please contact npg@nature.com

Figure 1

Partial reduction of heteroaromatic compounds (dr = diastereomeric ratio).

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Figure 2

Birch reduction mechanism.

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Figure 3

Example procedures of partial reduction methodology.

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Figure 4

Equipment set-up for addition of lithium (Step 1B(vi)).

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Figure 5

Formation of LiDBB showing characteristic blue/green color (Step 1B(vii)).

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Figure 6

Grinding of the lithium into a fine grey powder (Step 1C(v)).

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Figure 7

Transfer of THF to the lithium powder showing characteristic blue/green color of LiDBB solution (Step 1C(vi)).

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Table 1

Troubleshooting table.

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