Zn- and Cu-Catalyzed Coupling of Tertiary Alkyl Bromides and Oxalates to Forge Challenging C–O, C–S, and C–N Bonds
- Resource Type
- Authors
- Zhaodong Zhu; Hegui Gong; Weiqi Tong; Yuxin Gong; Qun Qian
- Source
- Organic Letters. 23:1005-1010
- Subject
- chemistry.chemical_classification
Steric effects
010405 organic chemistry
Organic Chemistry
010402 general chemistry
01 natural sciences
Biochemistry
Medicinal chemistry
0104 chemical sciences
Catalysis
Lewis acid catalysis
chemistry.chemical_compound
chemistry
Phenols
Physical and Theoretical Chemistry
Alkyl
- Language
- ISSN
- 1523-7052
1523-7060
We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)2-catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)2-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp3)-heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.