Isocyanides as Acceptor Groups in MHAT Reactions with Unactivated Alkenes

Area of Science:

• Organic Chemistry
• Synthetic Methodology
• Heterocyclic Chemistry

Background:

• Metal-hydride hydrogen atom transfer (MHAT) reactions are valuable for C-C bond formation.
• Isocyanides are versatile building blocks in organic synthesis.
• Efficient synthesis of substituted heterocycles remains a key challenge.

Purpose of the Study:

• To develop a novel method for synthesizing heterocycles using isocyanides.
• To explore the application of MHAT coupling reactions with isocyanides and nonactivated alkenes.
• To demonstrate the broad utility of the developed methodology for various heterocyclic scaffolds.

Main Methods:

• Utilized isocyanides as acceptor groups in MHAT coupling reactions.
• Employed direct coupling and cyclization for monosubstituted alkenes.
• Developed a two-step, one-pot procedure (MHAT reductive cyclization followed by MHAT Minisci coupling) for more substituted alkenes.

Main Results:

• Successfully coupled and cyclized monosubstituted alkenes directly.
• Achieved synthesis of diverse substituted heterocycles, including phenanthridines, indoles, and isoquinolines.
• Demonstrated the versatility of the MHAT coupling and Minisci coupling sequence for complex substrates.

Conclusions:

• The described methodology provides an efficient route to substituted heterocycles.
• Isocyanides serve as effective acceptor groups in MHAT coupling reactions for heterocycle synthesis.
• The developed two-step procedure expands the scope of MHAT reactions for complex alkene substrates.