Organolithium compound | Wikipedia audio article
Channel: Subhajit Sahu
Date: 15/01/2019

This is an audio version of the Wikipedia Article:
https://en.wikipedia.org/wiki/Organolithium_reagent


00:01:01 1 History and development
00:01:37 2 Structure
00:02:16 2.1 Nature of carbon-lithium bond
00:03:20 2.2 Solid state structure
00:06:13 2.3 Solution structure
00:08:16 2.4 Structure and reactivity
00:11:09 3 Reactivity and applications
00:11:51 3.1 As nucleophile
00:12:01 3.1.1 Carbolithiation reactions
00:14:06 3.1.2 Addition to carbonyl compounds
00:17:50 3.1.3 SsubN/sub2 type reactions
00:18:50 3.2 As base
00:19:10 3.2.1 Metalation
00:19:58 3.2.1.1 Superbases
00:23:21 3.2.1.2 Asymmetric metalation
00:24:03 3.2.2 Enolate formation
00:24:48 3.3 Lithium-halogen exchange
00:27:25 3.4 Transmetalation
00:31:58 4 Preparation
00:33:21 4.1 Reaction with lithium metal
00:33:48 4.2 Metalation
00:35:01 4.3 Lithium halogen exchange
00:36:03 4.4 Transmetalation
00:36:52 4.5 Shapiro reaction
00:37:15 5 Handling
00:37:36 6 See also
00:38:28 7 References



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SUMMARY
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Organolithium reagents are organometallic compounds that contain carbon – lithium bonds. They are important reagents in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C-Li bond is highly ionic. Owing to the polar nature of the C-Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.