Organic Chemistry Laboratory, Nagoya University

Haruka Omachi, Sanae Matsuura, Yasutomo Segawa, and Kenichiro Itami

Angew. Chem. Int. Ed. 2010, Early View. DOI: 10.1002/anie.201005734

A modular strategy served in the size-selective syntheses of [14]-, [15]-, and [16]cycloparaphenylenes (CPPs). A Suzuki–Miyaura coupling was used to assemble a terphenyl-equivalent, L-shaped cis-1,4-diphenylcyclohexane unit and a linear benzene/biphenyl unit in a 3+1+3 or 3+2+3 mode to give U-shaped septi- and octiphenyl units. The cyclizative dimerization of these U-shaped units and subsequent aromatization yielded the CPPs.