The 4.5 year academic–industrial collaboration between the process chemistry group at Lilly and the Stephenson group (Boston University and University of Michigan) is summarized. From the industrial perspective, the relationship benefitted Lilly by enabling the development of visible-light photoredox catalysis processes with an expert partner as well as the establishment of internal technology platforms to support such processes. In addition to the funding element, the academic side benefited from the ability to access pharmaceutically relevant problems and tap into continuous processing capabilities at Lilly. Another positive outcome of the collaboration was the inspiration of spinoff projects, which themselves generated substantial value in the academic setting. The postdoctoral researchers involved benefitted from the unique mentorship opportunity provided by the collaboration and access to resources from both academia and industry. We will analyze the impact of the collaboration in terms of personal development, publications, and new technologies that resulted, which we feel were highly beneficial for both sides of the collaboration.

A simple method for accessing trans‐2,3‐diaryl dihydrobenzofurans is reported. This approach leverages the equilibrium between quinone methide dimers and their persistent radicals. This equilibrium is disrupted by phenols that yield comparatively transient phenoxyl radicals, leading to cross‐coupling between the persistent and transient radicals. The resultant quinone methides with pendant phenols rapidly cyclize to form dihydrobenzofurans (DHBs). This putative biomimetic access to dihydrobenzofurans provides superb functional group tolerance and a unified approach for the synthesis of resveratrol‐based natural products.

A simple method for accessing trans-2,3-diaryl-dihydrobenzofurans is reported. This approach leverages a persistent radical equilibrium between quinone methide dimers and the persistent phenoxyl radicals derived therefrom. This equilibrium is disrupted by phenols that yield transient phenoxyl radicals, leading to cross-coupling between persistent and transient radicals. The resultant quinone methides with pendant phenols rapidly cyclize to dihydrobenzofurans (DHBs). This putatively biomimetic access to dihydrobenzofurans provides superb functional group tolerance and a unified approach for the synthesis of resveratrol-based natural products.

A simple method for accessing trans-2,3-diaryl-dihydrobenzofurans is reported. This approach leverages a persistent radical equilibrium between quinone methide dimers and the persistent phenoxyl radicals derived therefrom. This equilibrium is disrupted by phenols that yield transient phenoxyl radicals, leading to cross-coupling between persistent and transient radicals. The resultant quinone methides with pendant phenols rapidly cyclize to dihydrobenzofurans (DHBs). This putatively biomimetic access to dihydrobenzofurans provides superb functional group tolerance and a unified approach for the synthesis of resveratrol-based natural products.

A simple method for accessing trans‐2,3‐diaryl dihydrobenzofurans is reported. This approach leverages the equilibrium between quinone methide dimers and their persistent radicals. This equilibrium is disrupted by phenols that yield comparatively transient phenoxyl radicals, leading to cross‐coupling between the persistent and transient radicals. The resultant quinone methides with pendant phenols rapidly cyclize to form dihydrobenzofurans (DHBs). This putative biomimetic access to dihydrobenzofurans provides superb functional group tolerance and a unified approach for the synthesis of resveratrol‐based natural products.