Reference

Trimethylsilyl (TMS) groups are commonly used as protecting groups for alcohols in organic synthesis. Various acids can effectively cleave TMS groups from protected molecules. Here's a summary of the acids known to cleave TMS groups:

1. Acetic Acid: Acetic acid in aqueous conditions is effective in cleaving TMS groups.

   • Source: ScienceDirect

2. Hydroiodic Acid (HI): Hydroiodic acid is a particularly strong acid used for ether cleavage, including TMS-protected alcohols.

   • Source: Master Organic Chemistry

3. Trifluoroacetic Acid (TFA): Trifluoroacetic acid is also used to cleave TMS groups.

   • Source: Wikipedia

4. Hydrochloric Acid (HCl): A dilute solution of hydrochloric acid can similarly cleave TMS ethers.

   • Source: Gelest

In summary:

• Acetic Acid (commonly in water/tetrahydrofuran solutions)
• Hydroiodic Acid (HI)
• Trifluoroacetic Acid (TFA)
• Hydrochloric Acid (HCl) (dilute solutions)

Each of these acids offers different reaction conditions that can be chosen based on the sensitivity of the substrate and the desired rate of deprotection.