Applications Carbon–hydrogen bond activation

1 applications

1.1 natural gas
1.2 natural product synthesis

1.2.1 (+)-lithospermic acid via c-h activation
1.2.2 calothrixin , b via c-h activation
1.2.3 mescaline analogue via c-h activation

applications

no applications have been commercialized homogeneously catalyzed c-h activations.

natural gas

naturally occurring methane not utilized chemical feedstock, despite abundance , low cost. current technology makes prodigious use of methane steam reforming produce syngas, mixture of carbon monoxide , hydrogen. syngas used in fischer-tropsch reactions make longer carbon chain products or methanol, 1 of important industrial chemical feedstocks. intriguing methods convert these hydrocarbons involves c-h activation. periana, example, reported complexes containing late transition metals, such pt, pd, au, , hg, react methane (ch4) in h2so4 yield methyl bisulfate. process has not been implemented commercially.

natural product synthesis

the development of methodology c-h activation has impacted natural product synthesis, @ least in academic realm. ideally, synthetic routes contain minimal steps, while maximizing yield. c-h activation has enabled researchers activate c-h bonds in highly functionalized molecules.

the product in above reaction common scaffold multiple natural products, including hapalindole q , ambiguine h. core structure can made through c-c bond (blue bond in product) formation via c-h activation. innate reactivity of indole , enolate leads formation of c-c bond form indole-carvone intermediate.

(+)-lithospermic acid via c-h activation

the total synthesis of lithospermic acid employs guided c-h functionalization late stage highly functionalized system. directing group, chiral nonracemic imine, capable of performing intramolecular alkylation, allows rhodium-catalyzed conversion of imine dihydrobenzofuran.

calothrixin , b via c-h activation

the total synthesis of calothrixin , b features intramolecular pd-catalyzed cross coupling reaction via c-h activation, example of guided c-h activation. cross coupling occurs between aryl c-i , c-h bonds form c-c bond (highlighted in red).

mescaline analogue via c-h activation

the synthesis of mescaline analogue, has interesting biological properties, employs, specifically, rhodium-catalyzed enantioselective annulation of aryl imine via c-h activation.