Tertiary Alkylative Suzuki–Miyaura Couplings

Naoki Tsuchiya; Tom D. Sheppard; Takashi Nishikata

doi:10.1055/a-1732-4597

Synthesis, Table of Contents

Synthesis 2022; 54(10): 2340-2349
DOI: 10.1055/a-1732-4597

short review

Tertiary Alkylative Suzuki–Miyaura Couplings

Authors

Naoki Tsuchiya

^aGraduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan
Tom D. Sheppard ∗

^bDepartment of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London, WC1H 0AJ, UK
Takashi Nishikata ∗

^aGraduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan

Abstract

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Abstract

Suzuki–Miyaura coupling is an extremely useful way to construct Csp²–Csp² carbon bonds. On the other hand, Csp²–Csp³ coupling reactions do not work well, and tert-alkylative Suzuki–Miyaura coupling is particularly challenging due to problematic oxidative addition and β-hydride elimination side reactions. In this short review, we will introduce recent examples of tert-alkylative Suzuki–Miyaura couplings with tert-alkyl electrophiles or -boron reagents. The review will mainly focus on catalyst and product structures and on the proposed mechanisms.

1 Introduction

2 Ni-Catalyzed tert-Alkylative Couplings

3 Pd-Catalyzed tert-Alkylative Couplings

4 Fe-Catalyzed tert-Alkylative Couplings

5 tert-Alkylative Couplings with 1-Alkenyl Borons

6 tert-Alkylative Couplings under Photoirradiation

7 Stereospecific tert-Alkylative Couplings

8 Conclusion

Key words

radical - tert-alkyl - Suzuki–Miyaura coupling - SET - stereospecific reactions

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References

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