TY - JOUR
T1 - Stereospecific Stille Cross-Couplings Using Mn(II)Cl2
AU - Dakarapu, Rambabu
AU - Falck, J R
N1 - Funding Information:
Financial support provided by the Dr. Ralph and Marian Falk Medical Research Trust, Bank of America, N.A., Trustee, the Cystic Fibrosis Foundation (HURLEY16G0), NIH (RO1 HL111392), and the Robert A. Welch Foundation (Grant I-0011).
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/2/2
Y1 - 2018/2/2
N2 - Cross-coupling reactions are a staple in organic synthesis, especially for C-C bond formation with sp- and sp2-carbon electrophiles. In recent years, the range of accessible C-C bonds has been extended to stereogenic centers which expedites access to greater molecular complexity. However, these reactions predominantly depend upon late transition metal (LTM) catalysts whose cost, toxicity, and/or environmental impact have come under increasing scrutiny and governmental regulation. Here, we report Mn(II)Cl2 complexes alone, or with assistance from copper, catalyze the stereospecific cross-coupling of α-alkoxyalkylstannanes with organic electrophiles with complete retention of configuration.
AB - Cross-coupling reactions are a staple in organic synthesis, especially for C-C bond formation with sp- and sp2-carbon electrophiles. In recent years, the range of accessible C-C bonds has been extended to stereogenic centers which expedites access to greater molecular complexity. However, these reactions predominantly depend upon late transition metal (LTM) catalysts whose cost, toxicity, and/or environmental impact have come under increasing scrutiny and governmental regulation. Here, we report Mn(II)Cl2 complexes alone, or with assistance from copper, catalyze the stereospecific cross-coupling of α-alkoxyalkylstannanes with organic electrophiles with complete retention of configuration.
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U2 - 10.1021/acs.joc.7b02780
DO - 10.1021/acs.joc.7b02780
M3 - Article
C2 - 29320181
AN - SCOPUS:85041585317
SN - 0022-3263
VL - 83
SP - 1241
EP - 1251
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -