Journal
ORGANIC LETTERS
Volume 18, Issue 16, Pages 4088-4091Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01934
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Funding
- National Science Foundation of China [21202049]
- Recruitment Program of Global Experts (1000 Talents Plan)
- National Science Foundation of Fujian Province [2016J01064]
- Fujian Hundred Talents Plan
- Program of Innovative Research Team of Huaqiao University
- University of Illinois at Chicago
- Huaqiao University
- Fujian 100 Talents Plan
- Graduate Innovation Fund
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A mild, transition metal-free, dibotane-imediated deoxygenation of nitro groups was discovered that in situ generates nitrosoarene reactive intermediates. This new reactivity mode of B(2)pin(2) was leveraged to construct indoles from o-nitrostyrenes through a reductive-cyclization reaction that exhibits Hammett rho-value of +0.97 relative to sigma(para) values. Our new deoxygenation reaction is efficient, practical, and scaleable, enabling access to a broad range of indoles.
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