TY - JOUR
T1 - Practical and Modular Construction of C(sp3)-Rich Alkyl Boron Compounds
AU - Yang, Yangyang
AU - Tsien, Jet
AU - Ben David, Ayala
AU - Hughes, Jonathan M.E.
AU - Merchant, Rohan R.
AU - Qin, Tian
N1 - Funding Information:
Financial support for this work was provided by the Robert A. Welch Foundation (Grant I-2010–20190330) and the Eugene McDermott Scholar Endowed Scholarship. Green Fellow supported an undergraduate fellowship to A.B.D.
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2021/1/13
Y1 - 2021/1/13
N2 - Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method is extensively examined through a variety of substrates, including synthesis and late-stage functionalization of scaffolds relevant to medicinal chemistry. The strategic significance of this approach, with alkyl boronic acids as linchpins, is demonstrated through various downstream functionalizations of the alkyl boron compounds. This two-step concurrent cross-coupling approach, resembling formal and flexible alkyl-alkyl couplings, provides a general entry to synthetically challenging high Fsp3-containing drug-like scaffolds.
AB - Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method is extensively examined through a variety of substrates, including synthesis and late-stage functionalization of scaffolds relevant to medicinal chemistry. The strategic significance of this approach, with alkyl boronic acids as linchpins, is demonstrated through various downstream functionalizations of the alkyl boron compounds. This two-step concurrent cross-coupling approach, resembling formal and flexible alkyl-alkyl couplings, provides a general entry to synthetically challenging high Fsp3-containing drug-like scaffolds.
UR - http://www.scopus.com/inward/record.url?scp=85099108027&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85099108027&partnerID=8YFLogxK
U2 - 10.1021/jacs.0c11964
DO - 10.1021/jacs.0c11964
M3 - Article
C2 - 33347297
AN - SCOPUS:85099108027
SN - 0002-7863
VL - 143
SP - 471
EP - 480
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 1
ER -