Stereoselective Palladium-Catalyzed 1,3-Arylboration of Unconjugated Dienes for Expedient Synthesis of 1,3-Disubstituted Cyclohexanes
Pang, Hailiang; Wu, Dong; Cong, Hengjiang; Yin, Guoyin; ACS Catalysis 9 (2019) 8555–; doi:10.1021/acscatal.9b02747

data_4514824
_publ_section_title
;
 Stereoselective Palladium-Catalyzed 1,3-Arylboration of Unconjugated
 Dienes for Expedient Synthesis of 1,3-Disubstituted Cyclohexanes
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8555
_journal_paper_doi               10.1021/acscatal.9b02747
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C16 H20 O3'
_chemical_formula_sum            'C16 H20 O3'
_chemical_formula_weight         260.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-14
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 111.709(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.2814(16)
_cell_length_b                   6.1424(4)
_cell_length_c                   15.8248(9)
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.24
_cell_measurement_theta_min      3.04
_cell_volume                     2825.0(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7584
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        64.992
_diffrn_reflns_theta_max         64.992
_diffrn_reflns_theta_min         3.041
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6295
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2346
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0795
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1432P)^2^+1.5088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2344
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1953
_reflns_number_total             2346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02747_si_005.cif
_cod_data_source_block           cu_47_1i_0m
_cod_database_code               4514824
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2. Restrained distances 
 C3'-C2' 
 1.39 with sigma of 0.02 
 C4'-C5' 
 1.39 with sigma of 0.02 
 C6'-C5' = C6'-C1' 
 1.51 with sigma of 0.02 
 C4'-C3' = C2-C3 
 1.51 with sigma of 0.02 
 O1-C7 = O1'-C7' 
 1.42 with sigma of 0.02 
 C4-C3 = C4'-C5' 
 1.39 with sigma of 0.01 
 C8-C7 = C1'-C7' = C7-C1 = C2'-C1' = C2'-C3' 
 1.51 with sigma of 0.01 
 C8-C7 = C7-C1 = C2-C1 = C3-C2 = C5-C4 = C6-C5 = C6-C1 = C3'-C4' 
 1.51 with sigma of 0.01 
 C9-C8 
 1.45 with sigma of 0.01 
 C1-C3 = C1-C5 
 2.54 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim 
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) 
\\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C1') \\sim Ueq, Uanis(C2') \\sim Ueq, 
Uanis(C3') \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C5') \\sim Ueq, Uanis(C6') 
\\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(O1') \\sim Ueq, Uanis(C8) \\sim Ueq: 
with sigma of 0.01 and sigma for terminal atoms of 0.02 
Uanis(C4) = Uanis(C4') 
4. Others 
 Sof(H8BC)=Sof(H8BD)=Sof(C1')=Sof(H1')=Sof(C2')=Sof(H2'A)=Sof(H2'B)=Sof(C3')= 
 Sof(H3'A)=Sof(H3'B)=Sof(C4')=Sof(H4')=Sof(C5')=Sof(H5')=Sof(C6')=Sof(H6'A)= 
 Sof(H6'B)=Sof(C7')=Sof(H7')=Sof(O1')=Sof(H1'A)=1-FVAR(1) 
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)= 
 Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(H7)=Sof(H8AA)= 
 Sof(H8AB)=Sof(O1)=Sof(H1A)=FVAR(1) 
5.a Ternary CH refined with riding coordinates: 
 C1(H1), C7(H7), C1'(H1'), C7'(H7') 
5.b Secondary CH2 refined with riding coordinates: 
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C8(H8AA,H8AB), C8(H8BC,H8BD), C2'(H2'A, 
 H2'B), C3'(H3'A,H3'B), C6'(H6'A,H6'B) 
5.c Aromatic/amide H refined with riding coordinates: 
 C10(H10), C11(H11), C13(H13), C14(H14), C3(H3), C4(H4), C4'(H4'), C5'(H5') 
5.d Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C) 
5.e Idealised tetrahedral OH refined as rotating group: 
 O1(H1A), O1'(H1'A) 
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_olex2_submission_special_instructions 'No special instructions were received'