(CAAC)Copper Catalysis Enables Regioselective Three-Component Carboboration of Terminal Alkynes

Gao, Yang; Kim, Nana; Mendoza, Skyler D.; Yazdani, Sima; Faria Vieira, Andre; Liu, Mingyu; Kendrick, IV, Aaron; Grotjahn, Douglas B.; Bertrand, Guy; Jazzar, Rodolphe; Engle, Keary M.

doi:10.1021/acscatal.2c00614

(CAAC)Copper Catalysis Enables Regioselective Three-Component Carboboration of Terminal Alkynes

Journal Article · Thu Jun 02 00:00:00 EDT 2022 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.2c00614· OSTI ID:1905841

^[1]; Kim, Nana ^[2]; ^[2]; Yazdani, Sima ^[3]; Faria Vieira, Andre ^[4]; Liu, Mingyu ^[2]; Kendrick, IV, Aaron ^[2]; Grotjahn, Douglas B. ^[5]; Bertrand, Guy ^[4]; ^[4]; ^[2]

The Scripps Research Inst., La Jolla, CA (United States); UCSD
The Scripps Research Inst., La Jolla, CA (United States)
Univ. of California, San Diego, CA (United States). UCSD-CNRS Joint Research Lab.; San Diego State Univ., CA (United States)
Univ. of California, San Diego, CA (United States). UCSD-CNRS Joint Research Lab.
San Diego State Univ., CA (United States)

Here, cyclic(alkyl)(amino)carbene (CAAC) ligands are found to perturb regioselectivity of the copper-catalyzed carboboration of terminal alkynes, favoring the less commonly observed internal alkenylboron regiosomer through an α-selective borylcupration step. A variety of carbon electrophiles participate in the reaction, including allyl alcohols derivatives and alkyl halides. The method provides a straightforward and selective route to versatile tri-substituted alkenylboron compounds that are otherwise challenging to access.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, San Diego, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Institutes of Health (NIH); National Science Foundation (NSF); French National Research Agency (ANR)

Grant/Contract Number:: SC0009376

OSTI ID:: 1905841

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 12 Vol. 12; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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(CAAC)Copper Catalysis Enables Regioselective Three-Component Carboboration of Terminal Alkynes

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