期刊
ORGANIC PROCESS RESEARCH & DEVELOPMENT
卷 17, 期 1, 页码 29-39出版社
AMER CHEMICAL SOC
DOI: 10.1021/op300236f
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资金
- Boehringer Ingelheim
- Bristol-Myers Squibb
- DuPont
- Eli Lilly
- Amgen
- AstraZeneca
- NOBCChE/GlaxoSmithKline
- Roche
- A. P. Sloan Foundation
- University of California - Los Angeles
This review describes our laboratory's efforts to develop transition metal-catalyzed cross-couplings of several unconventional phenol-based electrophiles. Specifically, we highlight herein the following four key transformations: (a) nickel-catalyzed Suzuki Miyaura couplings of aryl pivalates, carbamates, and sulfamates to construct sp(2)-sp(2) C-C bonds; (b) iron-catalyzed Kumada couplings of aryl carbamates and sulfamates for the assembly of sp(2)-sp(3) C-C bonds; (c) nickel-catalyzed amination reactions of carbamates and sulfamates to build aryl C-N bonds; and (d) nickel-catalyzed reductive cleavage reactions of aryl carbamates to achieve aryl deoxygenation and a rare method for cine substitution. We expect this review will enable the greater use of unconventional phenol-based cross-coupling electrophiles in industrial settings.
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