Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 9, Pages 3223-3227Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b00881
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Funding
- TSRI
- Pfizer, Inc.
- Bristol-Myers Squibb
- National Institutes of Health [1R35GM125052]
- USTC
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM125052] Funding Source: NIH RePORTER
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A palladium(II)-catalyzed alkene difunctionalization reaction has been developed, wherein B(2)pin(2) is used to trap chelation-stabilized alkylpalladium(II) intermediates that are formed upon nucleopalladation. A range of carbon and nitrogen nucleophiles were found to be suitable coupling partners in this transformation, providing moderate to high yields. Both 3-butenoic and 4-pentenoic acid derivatives were reactive substrate classes, affording beta,gamma- and gamma,delta-difunctionalized carboxylic acid derivatives. This work represents a new strategy to synthesize highly functionalized secondary boronates that complements existing methods.
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