Mn-mediated reductive C(sp3)–Si coupling of activated secondary alkyl bromides with chlorosilanes

• Published in: Chinese chemical letters Vol. 33; no. 12; pp. 5061 - 5064
• Main Authors: Qi, Liangliang, Pang, Xiaobo, Yin, Kai, Pan, Qiu-Quan, Wei, Xiao-Xue, Shu, Xing-Zhong
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.12.2022; State Key Laboratory of Applied Organic Chemistry(SKLAOC),College of Chemistry and Chemical Engineering,Lanzhou University,Lanzhou 730000,China%School of Chemistry and Chemical Engineering,Southeast University,Jiangsu Optoelectronic Functional Materials and Engineering Laboratory,Nanjing 211189,China; Zhejiang Nanjiao Chemistry Co.,Ltd.,Shangyu Economic and Technological Development Zone,Shangyu 312369,China
• Subjects: Alkylsilanes; Chlorosilanes; Organophosphorus; Organosilanes; Reductive coupling; Sulfones; Organophosphorus; Chlorosilanes; Reductive coupling; Organosilanes; Sulfones; Alkylsilanes
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2022.03.070

The construction of secondary alkylsilanes is a challenging subject in the synthetic community. The cross-coupling provides a practical solution to address this problem, but it typically relies on organometallic species. Herein, we report an Mn-mediated reductive C(sp3)–Si coupling to synthesize these compounds from alkyl and silyl electrophiles. This approach avoids the requirement for activation of Si–Cl by transition metals and thus allows for the coupling of various common chlorosilanes. The reaction proceeds under mild conditions and shows good functional group compatibility. The method offers access to α-silylated organophosphorus and sulfones with a scope that is complementary to those obtained from the established methods. We report here an Mn-mediated reductive C(sp3)–Si bond-forming reaction of alkyl and silyl halides. The reaction proceeds under mild conditions and works with various common chlorosilanes. This method offers a new approach for the synthesis of α-silylated organophosphorus and sulfones with a scope that is complementary to those obtained from the established methods. [Display omitted]