Camera-enabled techniques for organic synthesis

• Steven V. Ley,
• Richard J. Ingham,
• Matthew O’Brien and
• Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

• setup that might not otherwise be available. Suzuki–Miyaura reaction performed within a microfluidic system. The product is observed by high-speed microscope photography, which shows a precipitate forming within the microdroplets. Friedel–Crafts reactions performed by using solid-acid catalysis at high

Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles

• Peter Wipf and
• Marija D. Manojlovic

Beilstein J. Org. Chem. 2011, 7, 824–830, doi:10.3762/bjoc.7.94

• , the utility of the hydrozirconation of nitriles can be enhanced by using Lewis acids to engage nitrile-derived acylimines in Friedel–Crafts reactions, generating indanyl or tetrahydronaphthyl derivatives [34][35]. Previous work in our group had concentrated on the transmetalation of alkenyl- and

When cyclopropenes meet gold catalysts

• Frédéric Miege,
• Christophe Meyer and
• Janine Cossy

Beilstein J. Org. Chem. 2011, 7, 717–734, doi:10.3762/bjoc.7.82

• gold complexes involve intramolecular Friedel–Crafts reactions and the addition of carbonyl groups. Intramolecular Friedel–Crafts reactions In the context of their studies on the Lewis acid-catalyzed rearrangement of strained three-membered ring hydrocarbons, such as methylenecyclopropanes and

• with traces of water) should favour the formation of the more stable cyclopropyl cation 23. Afterwards, ring-opening and intramolecular Friedel–Crafts reactions should enable the formation of indene 20 or naphthalene 21. With the gold catalyst, the formation of indene 19 indicated that electrophilic

• in competition with Friedel–Crafts reactions Besides the gold-catalyzed intermolecular addition of alcohols to cyclopropenes, Lee et al. investigated the behaviour of methyl 3-arylcyclopropen-2-yl carboxylates to ascertain whether the organogold species resulting from the ring-opening in the presence

Molecular rearrangements of superelectrophiles

• Douglas A. Klumpp

Beilstein J. Org. Chem. 2011, 7, 346–363, doi:10.3762/bjoc.7.45

• developed. Among the useful Friedel–Crafts reactions, a large number of cyclizations have been developed, including efficient routes to heterocyclic systems [12]. Several reports have also described superelectrophiles participating in concerted reactions, such as the Nazarov cyclization [13]. Because

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

• Magnus Rueping and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

• undertaken in the last decade with catalytic FC alkylations, there are still major challenges that need addressing. To the best of our knowledge no catalytic enantioselective Friedel–Crafts reactions leading to enantioenriched 1,1-diarylalkanes are known. Chiral, bifunctional Lewis- or Brønsted acid

• would allow the use of the Friedel–Crafts reactions in the late stages of complex natural product synthesis or in the preparation of biological relevant molecules, including pharmaceuticals and agrochemicals. Furthermore, the extension of substrate scope away from π-activated alcohols and double bonds