Abstract

The catalytic double hydrometalation such as hydrosilylation and hydroborylation of organonitriles has attracted considerable attention because the obtained products are widely used in organic synthesis and it is thought to be one of the effective methods for reduction of organonitriles. However, the examples of these reactions are quite limited to date. This paper summarizes the development of selective double hydrosilylation, double hydroborylation, and dihydroborylsilylation of organonitriles, including their reaction mechanisms and the role of the metal species in the catalytic cycle.

Highlights

  • The catalytic hydrosilylation and hydroborylation of the carbon-nitrogen triple bond (C≡N bond) in organonitriles is becoming important in the synthetic chemistry

  • Examples of catalytic double hydrometalation of the carbon-nitrogen triple bond (C≡N bond) in organonitriles are limited: one example of Fe [12], Pt [17], Ir [18], and Ru [19], two examples of Co [20,21], four examples of Rh [22,23,24,25], and main group elements and fluoride [13,26,27,28] for double hydrosilylation and one example of Mg [29], Co [30], and Ni [31], and two examples of Ru [32,33] and Mo [34,35] for double hydroborylation have been reported to date

  • Based on the results mentioned above, we proposed a tentative catalytic cycle for the double hydrosilylation, double hydroborylation, and dihydroborylsilylation of organonitriles in the

Read more

Summary

Introduction

The catalytic hydrosilylation and hydroborylation of the carbon-nitrogen triple bond (C≡N bond) in organonitriles is becoming important in the synthetic chemistry. Examples of catalytic double hydrometalation of the carbon-nitrogen triple bond (C≡N bond) in organonitriles are limited: one example of Fe [12], Pt [17], Ir [18], and Ru [19], two examples of Co [20,21], four examples of Rh [22,23,24,25], and main group elements and fluoride [13,26,27,28] for double hydrosilylation and one example of Mg [29], Co [30], and Ni [31], and two examples of Ru [32,33] and Mo [34,35] for double hydroborylation have been reported to date

Double Hydrosilylation of Organonitriles
Intermediates andgenerated
Ru-catalyzed
Rh-catalyzed
Reductions
Homobimetallic
Plausible
Double
Double Hydroborylation of Organonitriles
12. Plausible
13. Ru-catalyzed
14. Double
Oxidative addition of reduction
Dihydroborylsilylation of Acetonitrile
On release of one carbonyl ligand
18. Proposed
Conclusions
Full Text
Paper version not known

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call

Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.