Wen, JW (Wen, Jiangwei)^{[ 1 ]} ; Zhang, F (Zhang, Fan)^{[ 1 ]} ; Shi, WY (Shi, Wenyan)^{[ 1 ]} ; Lei, AW (Lei, Aiwen)^{[ 1,2 ]}

The functionalization of internal olefins has been a challenging task in organic synthesis. This protocol provides an efficient and transition-metal-free direct oxidative C(sp(2))-H/C(sp(3))-H cross-coupling method to access tetrasubstituted olefins. The push-pull effect from the polarized olefin substrates accelerates the internal olefin C-H alkylation. Importantly, the mechanistic experimental results demonstrate that the alkanes C-H bond cleavage is the rate-determining step, and a radical pathway has been proposed for the alkylation reaction. Notably, the present protocol has excellent functional group tolerance and could be easily scaled up with good efficiency.

作者关键词:alkylation; C-H activation; internal olefins; metal-free; cross-coupling

KeyWords Plus:RADICAL CYCLIZATION CONDITIONS; 6-MEMBERED HETEROCYCLIC RINGS; C-H BONDS; DIRECT ALKENYLATION; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; HECK REACTION; FUNCTIONALIZATION; ACTIVATION; ALKANES

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, Coll Chem & Mol Sci, IAS, Wuhan 430072, Hubei, Peoples R China.

Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognizat & Funct, Inst Chem, Beijing 100190, Peoples R China.

地址:

电子邮件地址:aiwenlei@whu.edu.cn

原文PDF链接：

https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201701664