Highly scalable photoinduced synthesis of silanols via untraversed pathway for chlorine radical (Cl•) generation

Argha Saha, Wajid Ali, Daniel B. Werz () and Debabrata Maiti ()
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Argha Saha: Indian Institute of Technology Bombay
Wajid Ali: Indian Institute of Technology Bombay
Daniel B. Werz: Institute of Organic Chemistry
Debabrata Maiti: Indian Institute of Technology Bombay

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract The emergence of visible light-mediated synthetic transformations has transpired as a promising approach to redefine traditional organic synthesis in a sustainable way. In this genre, transition metal-mediated photoredox catalysis has led the way and recreated a plethora of organic transformations. However, the use of photochemical energy solely to initiate the reaction is underexplored. With the direct utilization of photochemical energy herein, we have established a general and practical protocol for the synthesis of diversely functionalized organosilanols, silanediols, and polymeric siloxanol engaging a wide spectrum of hydrosilanes under ambient reaction conditions. Streamlined synthesis of bio-active silanols via late-stage functionalization underscores the importance of this sustainable protocol. Interestingly, this work also reveals photoinduced non-classical chlorine radical (Cl•) generation from a readily available chlorinated solvent under aerobic conditions. The intriguing factors of the proposed mechanism involving chlorine and silyl radicals as intermediates were supported by a series of mechanistic investigations.

Date: 2023
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DOI: 10.1038/s41467-023-43286-z

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