What question did this study set out to answer?

To establish a direct, mild iron-catalyzed cross-coupling strategy to synthesize all-carbon 1,3-disubstituted bicyclo[1.1.1]pentanes using tertiary iodides as electrophilic partners.

April 28, 2020Angewandte Chemie International EditionOpen Access

Synthesis of All‐Carbon Disubstituted Bicyclo1.1.1pentanes by Iron‐Catalyzed Kumada Cross‐Coupling

View Full Paper

Ask AI

Bookmark

Authors

JNJeremy NugentUniversity of Oxford BSBethany R. ShireUniversity of Huddersfield DCDimitri F. J. CaputoUniversity of Oxford

Discussion

Member takes

Implication

Experimental methodology demonstrates efficient iron-catalyzed Kumada cross-coupling of iodo-bicyclo[1.1.1]pentanes with Grignard reagents, expanding access to valuable drug surrogates.

Key Points

To establish a direct, mild iron-catalyzed cross-coupling strategy to synthesize all-carbon 1,3-disubstituted bicyclo[1.1.1]pentanes using tertiary iodides as electrophilic partners.
Coupled 1-iodo-bicyclo[1.1.1]pentanes with aryl and heteroaryl Grignard reagents using iron catalysis under mild conditions.
Evaluated reaction scope across diverse functionalized coupling partners and synthesized drug analogues.
Demonstrated the first general use of 1-iodo-bicyclo[1.1.1]pentanes as electrophiles and the first Kumada coupling of tertiary iodides.
Achieved broad functional group tolerance and short reaction times across a diverse library of 1,3-C-disubstituted bicyclo[1.1.1]pentane motifs.

Cite This Study

Nugent et al. (2020) studied this question.

synapsesocial.com/papers/6a86e16ba588a0bfb8beea58 https://doi.org/10.1002/anie.202004090

View Full Paper

Ask AI

Bookmark

Implication

Experimental methodology demonstrates efficient iron-catalyzed Kumada cross-coupling of iodo-bicyclo[1.1.1]pentanes with Grignard reagents, expanding access to valuable drug surrogates.

Synthesis of All‐Carbon Disubstituted Bicyclo1.1.1pentanes by Iron‐Catalyzed Kumada Cross‐Coupling

Discussion

Member takes

Implication

Key Points

Cite This Study

Synthesis of All‐Carbon Disubstituted Bicyclo1.1.1pentanes by Iron‐Catalyzed Kumada Cross‐Coupling

Discussion

Member takes

Implication

Key Points

Cite This Study

Also Consider

Also Consider