Catalytic 1,3-Proton Transfer in Alkenes Enabled by Fe=NR Bond Cooperativity: A Strategy for pKa-Dictated Regioselective Transposition of C=C Double Bonds

Gao, Yafei; Li, Xuelian; Stevens, Jeremiah E.; Tang, Hao; Smith, Jeremy M.

doi:10.1021/jacs.2c13350

Catalytic 1,3-Proton Transfer in Alkenes Enabled by Fe=NR Bond Cooperativity: A Strategy for pK_a-Dictated Regioselective Transposition of C=C Double Bonds

Journal Article · Thu May 25 00:00:00 EDT 2023 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c13350· OSTI ID:1991175

^[1]; Li, Xuelian ^[2]; ^[3]; ^[2]; ^[4]

Indiana University, Bloomington, IN (United States); Indiana University
Wenzhou University, Zhejiang (China)
The Ohio State University, Columbus, OH (United States)
Indiana University, Bloomington, IN (United States)

Transition metal catalyzed alkene double bond transposition usually involves metal hydride intermediates. Despite significant advances in the design of catalysts that dictate product selectivity, control over substrate selectivity is less advanced and transition metal catalysts that selectively transpose double bonds in substrates containing multiple 1-alkene functionalities are rare. Herein, we report that the three-coordinate high spin (S = 2) Fe(II) imido complex [Ph₂B(^tBuIm)₂Fe=NDipp][K(18-C-6)THF₂] (1-K(18-C-6)) catalyzes 1,3-proton transfer from 1-alkene substrates to afford 2-alkene transposition products. Mechanistic investigations involving kinetics, competition, and isotope labeling studies, supported by experimentally calibrated DFT computations, strongly support an unusual nonhydridic mechanism for alkene transposition that is enabled by the cooperative action of the iron center and basic imido ligand. As dictated by the pK_a of the allylic protons, this catalyst enables the regioselective transposition of C=C double bonds in substrates containing multiple 1-alkenes. The high spin (S = 2) state of the complex allows a wide scope of functional groups to be tolerated, including those that are typical catalyst poisons, such as amines, N-heterocycles, and phosphines. Furthermore, these results demonstrate a new strategy for metal-catalyzed alkene transposition with predictable substrate regioselectivity.

View Accepted Manuscript (DOE)

Research Organization:: Indiana University, Bloomington, IN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Zhejiang Provincial Natural Science Foundation of China

Grant/Contract Number:: SC0019466

OSTI ID:: 1991175

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 22 Vol. 145; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Catalytic 1,3-Proton Transfer in Alkenes Enabled by Fe=NR Bond Cooperativity: A Strategy for pKa-Dictated Regioselective Transposition of C=C Double Bonds

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Catalytic 1,3-Proton Transfer in Alkenes Enabled by Fe=NR Bond Cooperativity: A Strategy for pK_a-Dictated Regioselective Transposition of C=C Double Bonds