In the 1980s, while searching for new hydrocarbon activation catalysts, Crabtree's research group accidentally found that mercury vapour activated photochemically could perform some interesting and unusual alkane activation reactions yielding unusual products.

Some of the work is summarised in this Journal of Chemical Education paper from 1988. The reaction seems to be able to produce some unusual (and hard to get) dimers of hydrocarbons and is also tolerant of other functional groups (eg alcohols, amines) and can also generate cross coupled products (eg it will couple alcohols with hydrocarbons).

At the time it was thought to be an interesting curiosity but with some prospect of yielding easy routes to some hard-to-get targets.

Has it ever been used in a significant synthesis? Or for any industrial processes?

  • $\begingroup$ You will find that in general, use of photochemistry in commercial processes is rare as so few companies offer it as a service (as a CMO) and photochemistry is a pain in batch operations (due to efficiency and fouling). Also, due to trade secrets, certain companies might only release this technology information under confidentiality agreements. For these reasons, it would be hard to know for sure, but the probability is very small. $\endgroup$ – Beerhunter Oct 26 '17 at 18:15

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