Palladium-catalyzed Hiyama-type cross-coupling reactions of various arenesulfinates with organosilanes were achieved in good to excellent yields under aerobic conditions at 70 °C. Fluoride is essential, and tetrabutylammonium fluoride (TBAF) was shown to be the most efficient additive for these cross-coupling reactions. These cross-coupling reactions of the arenesulfinates provide high yields and show wide functional group tolerance, making them attractive alternative transformations to traditional cross-coupling approaches for carbon-carbon bond construction.

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Herein, we develop a new approach to directly access architecturally complex polycyclic indolines from readily available indoles and bicyclo[1.1.0]butanes (BCBs) through formal cycloadditions promoted by commercially available Lewis acids. The reaction proceeded through a stepwise pathway involving a nucleophilic addition of indoles to BCBs followed by an intramolecular Mannich reaction to form rigid indoline‐fused polycyclic structures, which resemble polycyclic indole alkaloids. This new reaction tolerated a wide range of indoles and BCBs, thereby allowing the one‐step construction of various rigid indoline polycycles containing up to four contiguous quaternary carbon centers.

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Palladium‐catalyzed cross‐coupling reactions of various aryl sulfinic acid salts with a wide variety of vinyl substrates have been achieved in good to excellent yields under simple aerobic conditions at 70°C with the assistance of Cu(II) salts. The reaction can be accelerated by the combination of DMSO with THF. The reported Matsuda–Heck type coupling reactions are tolerant to the common functional groups, making these transformations as attractive alternatives to the traditional cross‐coupling approaches. Copyright © 2013 John Wiley & Sons, Ltd.